


Devil's Row

by MissieFishie



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Basically every character makes an appearance, Explicit Sexual Content, F/F, F/M, Italian Mafia, M/M, Major character death - Freeform, Murderer!AU, Plaid Is The New Black, Plot Twist galore, Prison Escape, Prison Sex, Prison!Destiel, Prison!Sabriel, Prisoner!AU, Prisoner!Alastair, Prisoner!Dean, Prisoner!Gabriel, Prisoner!Lucifer, Rape, Russian Mafia, Supernatural - Freeform, dub-con, non-con, prison!au, prisoner!Sam, supernatural fanfic - Freeform, supernatural!AU
Language: English
Status: In-Progress
Published: 2014-07-30
Updated: 2016-11-18
Packaged: 2018-02-11 03:03:40
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Major Character Death, Rape/Non-Con
Chapters: 29
Words: 73,508
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2051106
Author URL: https://archiveofourown.org/users/MissieFishie/pseuds/MissieFishie
Summary: <blockquote class="userstuff">
              <p>After murderers Sam and Dean Winchester are caught red handed during a murder, they are found guilty and sentenced to 20 years in a high security prison called Folsom Prison. Enter Castiel Novak, the handsome yet harsh blue eyed Warden whom Dean decides to break and claim as his own to complete the final step in ensuring his status in the prison after his cell mate Alastair's escape. Alastair Heyerdahl tortures Dean and then proceeds to train him as his student, prepping the older Winchester to take the place of Alastair and his boss, when they leave. Sam enters willingly into a mutual beneficial relationship with his cell mate, Lucifer Pellegrino who is the head of the Italian Mafia, but when Sam meets con-artist Gabriel Speight, he struggles to find a way out of the dysfunctional relationship holding him back from being with the golden-eyed man of his dreams. Gabriel enlists his partner in crime, Fergus Crowley, to win back Sam's freedom from his crazed cell mate.</p><p> </p><p>For sneak peaks and random tidbits, as well as notifications of updates and random Supernatural Spams, follow my fandom account on Instagram: @iamsmauglocked // Tumblr: i-am-smaug-locked // Twitter: IAm_SmaugLocked // YouTube: Madeline Smaug</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I would like to thank my BETA Meg for being so amazing in struggling through this fic with me. I really couldn't have done this without you! You rock my socks!!

_Shit._

Dean heard the sirens long before the red and blue lights started flashing through the dirty warehouse windows. He looked down at the blonde woman sprawled out on the floor in front of him, blood pooled beneath her mangled body, her chest rising and falling so softly that if it weren't for the wheezing sound coming from her mouth he wouldn't know that she was still alive. He kneeled down next to her, smirking as her eyes widened; he could taste her fear, and he'd be lying if he said it wasn't a turn-on.

"Looks like our playtime is over, huh babe?" he chuckled, reaching his hand out to stroke her forehead gently. She whimpered and closed her eyes, trying to tilt her head away from Dean's palm. "Tsk tsk tsk, now that just won't do," he said, his voice turning into a growl as he grabbed her face and forced her to look at him. She whimpered again as he leaned the rest of the way down and pressed his lips against hers. He could feel her squirming underneath him, trying to get away, and he felt his smirk returning. He pulled away slowly, savoring the shaky breath she let out as he gently licked the tears streaming down her face. By this time the sirens were much closer; he estimated that he had about five minutes before the cops started beating down the doors. He stood and walked over to the table to retrieve his blade, jumping slightly as the door slammed open and Sam came running in.

"Dean, we have to move now. The cops are on their way and-" Sam looked down at the blonde and grimaced. "Why the hell isn't she dead yet?"

"Oh c'mon Sammy, loosen up and let me have some fun!" Dean teased as he stood sharpening his weapon.

"You've had your fun! We've been here for six hours now; it's a wonder the cops didn't arrive sooner," Sam retorted, taking long strides over to the window and peering out towards the main road. "It's time to end this Dean. Now."

"Fine." Dean crossed back to the woman, making sure to lock eyes with her before cupping her face and thrusting the knife deep into her chest. He kept looking long enough to see the lights leave her eyes and feel her head go limp in his hand. "Let's go."

They ran out the back to where their jet-black 1967 Chevrolet Impala was waiting patiently for their return. "Hey baby," Dean murmured, patting the dash as he slid into the driver's seat and started her up. Sam jumped into the passenger's side and slammed the door, yelling for Dean to hurry. They made it to the end of the driveway before finding themselves blocked in by cop cars. Dean cursed as he put the car into reverse and sped back the way they had just come. Unbeknownst to them, the police had decided to pull all the strings they could and there were more cop cars waiting just behind the building. Red and blue strobe lights lit their faces as Dean parked the car and turned to his little brother.  
  
"Sorry Sammy. I really screwed up this time, didn't I? It's the end of the line kiddo."

"Dean," Sam chuckled darkly, "I'm surprised at you! Giving up so soon? You're forgetting that we haven't been caught just yet." With that Sam cocked his pistol, and before Dean could say anything, he had jumped out of the car. Dean heard three shots and watched in horror as Sam fell to the ground.

"SAMMY!" he bellowed, launching himself out of the car and racing over to his brother's form.

"I'm okay," Sam groaned, his face a ghostly pale. "I'm okay Dean I promise. I just- just-" then he passed out cold in Dean's arms. Dean slowly grabbed his gun from his side, throwing it down in front of them; shaking, he raised his blood-stained hands to hold Sam's head to his chest and held them both up as best he could. Three cops made their way over to the two brothers. Two of them grabbed Sam and with the help of some paramedics, loaded him into an ambulance while the third cop cuffed Dean's hands behind his back.

"You have the right to remain silent. Anything you say can and will be held against you in the court of law. You have the right to an attorney. If you can not afford an attorney, one will be provided for you. Do you understand the rights I have just read to you? With these rights in mind, do you wish to speak to me?"

"Go to Hell."

 

 

 

 

\--------The Trial------

 

 

“How to the defendants plead?”

“Guilty your Honor.”

 

“Then by the power invested in me by the state of Kansas, I hereby sentence Dean Ross Winchester and Samuel Tristen Winchester to twenty years each in federal prison for the murder of Lilith McCormack as well as the murders of Kate Milligan and Adam Milligan along with the suspected murders of Bella Talbot, and John Winchester. They shall be kept under constant supervision in a high security ward. They will have no contact with the outer world for the first year of their sentence and there will be no bail. There will be no early release for good behavior and any fights they are involved with will be put on their record as federal offences. Court dismissed.”

 

Jess hissed and turned back to face Sam and Dean. “Raphael knows he’s the only judge for miles around who’s powerful enough to condemn you and he used that power to break rules to ensure that the two of you stay in prison the entirety of your sentence. I was originally going to suggest that you try for good behavior or see if there is anyway someone could help post bail but that son of a b-” Jess started cursing under her breath as she packed up her files.

 

If Sam was into women he would have found Jess very attractive. She had a nice form and was very well put together in both looks and mind. She recently graduated from Standford and had been appointed as their lawyer when Dean made it clear to the officers that they wouldn’t be able to afford a lawyer by themselves. More than once whilst prepping for the trial Dean had turned to Sam and given him a salacious wink, even going so far as to ask Jess if she’d be interested in a date. She turned him down by laughing and rolling her eyes as she walked away. Yes, if Sam were into women she would be the kind of woman he would end up marrying. Before their father’s death both Dean and Sam had had to hide their sexuality even from each other, and it wasn’t until Sam was seventeen and had come back to the hotel room early from dinner and found Dean with his dick shoved up some guys ass that Sam even knew his brother was going through a similar struggle. Dean hadn’t noticed that Sam was in the room until the younger Winchester cleared his throat pointedly, making Dean jump a foot in the air and fall off the bed. A few hours and a bottle of whiskey later, Dean explained to Sam that he wasn’t gay per-say, he simply enjoyed sex with guys as much as he did sex with girls and that men brought him just as much pleasure as women did and that for the love of god Sam can never mention any of this to John. Sam had nodded and told Dean that he understood the whole liking men thing because that’s all he ever liked. But then John had found out about Sam preferring men to women and shit had hit the fan.

“Your honor,” Jess’s voice drew Sam out of his memories, “Your honor, don’t you think that denial of bail and potential early release for good behavior is a little unconventional?”

 

“Unconventional? Did you read their files? They murder for fun. Just because they can. Because being in control gets them off. If anything, I’d say they got let off easy. If it were completely up to me, I’d have them both in their graves before dinner. See, I’ve had these two in and out of my courthouse for years now, murder charges, arson, robbery, kidnapping. I could never charge them for the things that I know they were behind because I lacked the required proof, but now, I’m just pleased that at least I finally have you locked up.” Raphael grinned down at the brothers, hatred in his eyes and a cocky look on his face that Dean would have thoroughly enjoyed knocking off with a blow or two, or twenty. He really wasn’t too picky as long as that smug bastard got put in his place. Dean growled and lunged for the Judge who sat back in his chair and laughed as the security guards hauled Dean out of the courtroom.

“Thank you your honor.” Jess sighed, and she walked ahead as Sam was escorted out of the courtroom, wondering what the next step was.


	2. Chapter 2

**Summary for the Chapter:**

> In which Sam and Dean go to prison where they meet their new cellmates, Lucifer Pellegrino and Alastair Heyerdahl.  
> We find out that Sam's cellmate, Lucifer, is the head of the Italian Mafia and that Dean's cellmate, Alastair, is Lucifer's second in command.  
> We also learn a little more about our two murderers and how they got to where they are today. 
> 
> Enjoy!

Sam and Dean’s arrival at Folsom Prison was met with wolf whistles and crude comments. Dean smirked the whole way to his cell, not at all bothered by the ass slaps and dirty praises of many of the sneering prisoners. Sam however was more than uncomfortable with the dirty,* grabby hands that seemed to be everywhere at once. He wasn’t used to being on the receiving end of such lustful desire and he knew that if any of these men decided to try and make good on the promises they were shouting out, he wouldn’t be able to stop them. After all, there was a very good reason he was the brains of the team and Dean was the punisher.

 _If I’m going to survive here_ , Sam thought, _I’m going to need to get in shape and learn a few things_.

To the brothers' horror, they were lead to separate cells on the opposite ends of the hall.

“What the fuck, where the Hell are you taking him? He’s supposed to be in the same cell as me,” Dean barked, trying to wrestle the guard's hands away.

“Not according to our instructions.” One of the guards laughed, shoving Dean forcefully into his cell. “Dean Winchester, meet Alastair Heyerdahl. Your cellmate.” With that, the cell door was slammed closed and locked. Dean heard a malicious chuckle waft down from the top bunk. He turned to look at the man laying there. He had a slender face and a crooked nose, and his cold blue eyes seemed to sink deep into his skull. His brown hair was cut short and his goatee framed his jaw and lips, which were curled into a smile that set the hairs on the back of Dean’s neck standing straight up.

“So…” Alastair drawled in a pinched voice, hopping lightly down from the bunk and gliding forward to stand mere inches away from Dean. “You’re my new student then I see.” He ran his index finger down Dean’s cheek; his grin widened when Dean flinched under the touch. “Oh you’ll do just fine.” He chuckled as he turned away from Dean and crossed to the far end of the jail cell. He reached under the mattress and pulled out a handcrafted knife.

“What do you mean ‘student’?” Dean hissed, his gaze never leaving the crude weapon in Alastair’s dirty hands.

“I’m going to teach you how to get ahead, how to not only survive in this hell hole, but how to thrive. If I heard correctly, you’ve got twenty years here. My boss and I are getting out real soon and we need someone to carry on our legacy. To work for us from the inside when we get out. We’re going to train you, prepare you to take over as the top dog, the head honcho.” He sauntered back over to Dean, his lanky body rigid and powerful. Instinctively Dean took a step away; he felt his back press into the cold metal of the door and a shudder ran up his spine as he watched his cellmate move slowly towards him. It had been ages since Dean had been the prey, he was always the predator, but Alastair’s power overtook his own. Dean closed his eyes and took a deep breath, his entire body freezing when he felt the knife on his neck. He willed himself to stay calm as he opened his eyes, finding himself nose to nose with Alastair whose thin lips were set in an ugly smile.

“You belong to me Winchester.” Alastair hissed, pressing the knife harder against Dean’s exposed throat. He bent his head down and licked the pulse point on Dean’s neck and Dean had to fight not to cry out at the unexpected, unwanted touch. He stood stock still as Alastair brought his mouth to his ear and whispered, “don’t forget who owns you here Dean. Follow my instructions and you will be respected, feared by all in this prison, this hell. However, if you disobey me, I will make sure you rot in here for twice as long as you’re supposed to. How does forty years in Hell sound to you Dean?”

“Not good.” Dean said his voice flat and his eyes dead. Alastair chuckled darkly in his ear before pulling away.

“That’s what I thought,” he laughed, and suddenly he sliced a clean cut running along Dean’s cheekbone. Dean hissed through the pain and backed even further into the cold door, pinching his eyes shut. “Now now pet, I want you to look at me during this. See, torture is one of the greatest pleasures life can give,” he cut another red line across Dean’s collarbone. “Seeing the blood escaping from your victim. Hearing their pain, the screams. Why won’t you scream for me Dean? Don’t you know it hurts my feelings that you won’t scream?” He dug the blade an inch into Dean’s thigh and twisted slightly. Dean let out a groan, his face contorting with anguish as he bit his tongue, refusing to give Alastair the pleasure of hearing him break. After all, he’d suffered worse in the past.

After his mother’s murder, his father had become more than just a drunk. He had become abusive. Dean had been beaten to the point of near death more times than he could count. It was all because he had his mother’s eyes and John couldn’t bear to see anything that reminded him of Mary. One night, an hour after Sam had gone to bed, Dean was finishing cleaning up from dinner when John had stormed into the house in a drunken rage, swearing up a storm and knocking over the furniture. Dean had hurried over to his father and begged him to be a little bit quieter because Sammy needed his sleep in order to be his best for his exam the next day. John had slapped him across the face so hard that he flew to the floor, his head cracking against the cold tile. John flipped Dean onto his back and started throwing punches anywhere he could reach. Dean could feel a warm liquid trickling through his hair and the tears that streamed from his eyes as he drifted in and out of consciousness, laying boneless on the floor while his father beat him into oblivion. He vaguely heard Sam’s voice shouting “DAD! DAD NO!” and remembered feeling the weight of John being suddenly absent, through swelling lids he watched in horror as John slammed a fist into Sam’s gut. Dean cried out as Sam crumpled unconscious to the floor. He forced himself up, rushing to the kitchen, dreading the sound of John’s footsteps racing up behind him. Dean had grabbed a knife from the counter and whirled around to face his father. He felt the blade sink into John’s stomach, he felt his father’s blood rushing out from around the knife, covering Dean’s hand and spilling onto the white linoleum kitchen floor. John’s eyes widened with surprise, and he clutched Dean’s shoulder as they both sunk slowly to the ground. “Take care of Sammy,” John choked out and Dean held him and he watched the lights leave his father’s eyes. Sam walked in some time later and found his older brother hunched over and sobbing into his father’s corpse, sitting in a pool of the older man’s blood. “Dean?” Sam gasped, running over to the pair and throwing his arms around Dean’s neck. There they stayed throughout the night, holding each other and crying until neither had any tears left. Dean had called Bobby the next morning while Sam was upstairs showering and had told him the entire story. Bobby arrived thirty minutes later, instructing Sam and Dean to pack their bags. Within an hour, they were on the road, John’s corpse wrapped in a carpet in the back of Bobby’s pick-up truck, Sam and Dean holding onto each other, afraid of what would happen if they let go. After leading the brothers to their new rooms, Bobby had taken John’s body out back and burned it. That night Dean’s dreams were filled with the feeling of the knife as it plunged into John’s stomach, the sight of the lights leaving his eyes, the smell of burning flesh, and the knowledge that Dean had murdered his own father.

Dean knew he could hold out on giving Alastair the satisfaction of hearing him scream for a little while longer. A fact he forgot as soon as he felt the knife carving up from his thigh to his rib cage. He threw back his head, hearing a faint crack as it slammed against the door. He yelled at the shooting pain running up his side and the aching throbbing in his head. He heard Alastair’s grating laughter as he continued to torture his latest victim.

 

On the opposite end of the Hall, Sam Winchester was doing his very best to ignore his cellmate, Lucifer Pellegrino, who seemed to have made it his personal mission to annoy the hell out of the younger Winchester.

“C’mon Sammy! Pay attention to me! I’m bored!” Lucifer whined from his bunk, a smile playing at the edge of his lips.

“Shut up.” Sam muttered, rolling his eyes and peering out the cell door, hoping to catch a glimpse of his older brother.

“He said, ‘Shut up’ to me.” Lucifer gasped, sarcasm dripping from his voice. Sam turned around and faced his cellmate, taking in the dirty blonde hair, bright blue eyes and sharp features that made up Lucifer’s face. He walked over to the wall opposite where Lucifer was lounging on his bed and sat down. They sat there in silence for a few minutes before the older man hopped down from the bed and sat next to Sam.

“Tell me about yourself boy.” He said, fidgeting with the ugly orange pant leg of his prison suit and then turning his eyes to Sam, who shifted uncomfortably under the gaze.

“Not much to tell.” Sam sighed. “My mother was murdered when I was a baby and my father was an abusive drunk. One night during one of his drunken beatings my brother stabbed him. We went on a few years without any issues, then one night we found out that our father had been cheating on our mother and Dean flipped. We drove to the woman’s house and he killed her and her son. That was kinda the beginning for us. Killing people, destroying lives, it’s become more or less the family business. It’s our personalized way to vent, to relieve our anger.” Sam gasped as Lucifer’s mouth pressed against his own. Lucifer used the gasp to slide his tongue into Sam’s mouth, exploring and claiming Sam as his own. He pinned Sam to the wall, straddling his lap and running his fingers through the long brunette locks.

“What- what are you doing?” Sam panted in between kisses, hands clasping Lucifer’s hips, pushing him away slightly.

“Relax. I know what I’m doing.” Pellegrino whispered, grabbing Sam’s face and pulling him in again, this time grinding his hips in time with the kiss.

Sam’s grasp on Lucifer’s hips became stronger as he guided the older man’s hips. “You know,” he murmured, “you never told me your back story.”

“I’m the head of the Italian mafia.”

Sam faltered and pulled back, looking at his cellmate with disbelief.

Lucifer chuckled. “I know right, not what you expected. I’m here on purpose though, if that makes you feel any better. My second in command, Alastair, and I needed to get on the inside to take care of… business. We’re out in a few weeks though, just as soon as we clear some things up and find a suitable successor to our roles here.”

Sam didn’t know if it would be safer to push the man off of him, or if he should instead pull him back into a greedy kiss. He wanted to do both, and found himself equally horrified and turned on by this powerful man still grinding in his lap, blue eyes dark with lust, fingers still entwined in his hair. He opted for the latter and before long the two men were groaning with guilty pleasure as they came together still fully clothed. They sat on the floor tangled together and panting until the guards started to make their evening rounds. Sam chuckled while he cleaned himself up when he heard Lucifer spewing vile, snarky comments at the guards as they walked passed. When it was Lucifer’s turn for the bathroom, Sam found himself returning the favor by shouting profanities aimed at a particularly lanky and timid guard named Garth. Garth did his very best to ignore Sam, but hurried out of the hallway as soon as the next guard came to relieve him.

That night Sam curled into his bed, surprisingly comfortable with where he was and what was happening. He could hear the gruff sound of a man being owned from somewhere down the hall, and he smirked as he thought of how helpless and pathetic that poor bastard was.

In his cell, Dean Winchester lay naked on his bed, his hands tied to the bedpost and his mouth gagged. Alastair was holding a knife to his throat with one hand and fondling Dean with his other. “Remember who you belong to Dean. I own you."


	3. Chapter 3

**Notes for the Chapter:**

> In which we meet Castiel. Chapter told from Dean's POV, then Cas's POV. 
> 
> Sorry Garth...
> 
> Oh and yay because Balthazar!

\---- Dean ----

“Dean, get up. It’s time to play. Don’t make me tell you again,” Alastair’s pinched voice whined from somewhere behind, and Dean felt a cold hand slide into his boxers.

Dean’s entire body hurt. For the past week Alastair had continuously used and abused him. He had several new physical scars accompanied by a few new mental ones. Alastair was a master of torture and each day he broke Dean into thousands of pieces, which he proceeded to break into thousands of smaller and smaller ones until by then end of their “session” Dean’s sturdy foundation had turned to dust. Dean belonged to Alastair and everyone in Folsom knew it. The only person who didn’t seem to give a shit was Sam’s cellmate, Lucifer, who didn’t even try to refrain himself from the occasional ass slap or forced kiss because according to him, “sharing is caring, and I AM Alastair’s boss after all. What he owns, I own.” At first, Dean tried to fight off Alastair, but he quickly learned that fighting only made things worse in the end. Deeper cuts, less prep combined with harder thrusts, but the worst torture of all was when Alastair would prep Dean and then go to bed, leaving Dean wide open and untouched. Those nights Dean hadn’t slept at all, stuck waiting for Alastair to hop down from the top bunk and finish the job. The first time this happened, Dean ended up finishing himself off. He was punished five minutes later by Alastair flipping him over and ramming his fingers into Dean’s ass and hitting that spot again and again until Dean came for a second time. Then while Dean was still recovering, Alastair shoved himself into Dean and positioned himself so that with each slow thrust, he dragged over Dean’s prostate,  gently pulling and rubbing Dean’s sac as he bit and sucked on Dean’s neck just below his jaw. Dean had come three times in an hour that night and he considered it the worst hour of his life.

Now here Alastair was again. Like he was every morning. Dean could feel the older man’s erection as he ground slowly into Dean’s abused ass. Last night had been particularly rough because Alastair had been forced to watch as Lucifer shoved his tongue down Dean’s throat, and even though Lucifer was his boss, Dean could tell Alastair didn’t like the idea of sharing. Dean let out a small sigh of relief when Alastair got up and walked out of the cell. “Come along dearie. Time for breakfast,” he called over his shoulder as he turned the corner, leaving Dean alone curled up in his bed, hoping that no one would come in and disturb him.

“Winchester. You need to get out to breakfast,” a voice demanded from the doorway.

Dean turned and saw the young, lanky guard named Garth staring at him, baton in hand, attempting to make himself appear larger than he really was. Dean snorted as he lazily sat up, still eyeing the guard. “What’s it to you whether I go to breakfast or not?”

“Honestly, I don’t give a shit. Nevertheless, it’s the rules. You don’t eat enough, you starve, you starve, you die, you die, and then my boss has a crap ton of paperwork to sort through and us guards get the bad end of his exhaustion. So for all our sakes, the rule is that prisoners have to eat three meals a day. No exceptions.”

“Well then it looks like you’re gunna have to break that rule, because I’m not going out there. I’m perfectly fine staying in my bed,” Dean stated defiantly as he flopped back onto the uncomfortable mattress. The guard was on him in a flash, giving him a solid whack with the baton and pulling on his hair until the prisoner stood up. Growling, Dean reared on the gangly man, snatching the baton from his slender fingers and shoving him up against the wall. He heard a crack and watched as the guard slid down to the floor. Dean wasn’t sure if the man was dead or simply unconscious, but he knew better than to wait around for another guard to find him. He turned for the door and was greeted by a man in a dark suit, wearing a white shirt and a bright blue tie that matched his eyes. His chapped lips were turned downwards and his head was cocked slightly to one side. He squinted at Dean and then swiftly moved past the prisoner to check on Garth.

“Lucky for you, he’s only been knocked out.” The man’s voice was raspy, as if he gurgled with gravel, but behind the initial roughness, Dean heard a tenderness and he watch as the man turned back to face him. “That was very stupid of you.”

“Yeah well what can I say? Reckless is my middle name.” Dean smirked, watching as the man’s frown deepened. 

“I said ‘stupid’, not ‘reckless’. And I don’t care what your middle name is. Why aren’t you at breakfast?” the man with the bright blue eyes asked, his eyebrows knit together in genuine confusion.

“Not hungry,” Dean replied, “but I bet you and I could think of a few things that might work up my appetite.” He grinned and winked salaciously, raking his eyes up and down the suited man’s form. He had a nice build, thin but not boney or lanky like the unconscious guard; Dean had no doubts that this mystery man secretly had the body of a god underneath his layers and Dean wanted to undress him and find out just how godlike he was. The man had a sharp jaw line accented by the dark stubble that grew around his jaws and lips. His dark brown hair stuck up in the front in a styled mess and Dean longed to run his fingers through it while kissing the man’s plump chapped lips. He took a step forward, a glint in his eye and a tent forming in his trousers, but he stopped his advance when the man raised a Taser.

“You should think carefully before making another move,” the man said, eyes cold. “I will not hesitate to use this should a display of force be required.”

Dean eyed the man carefully and then it clicked, “you’re the warden.” It was a statement, not a question and as soon as he said it, he knew that he was right.

“And you’re a murderer who just knocked out one of my guards because you didn’t want to go to breakfast,” the warden responded coolly.

“Well, you should find better guards. It hardly took me any effort to take him down.” Dean said, laughing as the scowl returned to the other man’s face. “You never told me what your name is.”

The warden bent over and in one swift move, he hauled the unconscious guard over his shoulders. When he reached the door he turned around and looked Dean up and down before saying, “My name is Castiel Novak, and unless you want to be tasered when I get back, I suggest that you go to the cafeteria and get some breakfast. Oh and Mr. Winchester,” he squinted again as he shifted Garth’s weight, “the next time you knock out one of my men, I will be forced to punish you and move you into isolation for a week.” With that, the warden was gone.

Dean stepped out the door and leaned up against the frame, watching as the warden made the journey down the hall to the infirmary, stopping every few feet to shift the weight of the unconscious Garth. “Castiel Novak huh, well Cas, if you promise to punish me then I promise to be on my very worst behavior.” He said to himself, absentmindedly licking his lips as he enjoyed the view of the warden’s behind before he turned and started to make his way to the cafeteria.

 

\---- Castiel ----

 

 

Castiel got up from his desk and began his usual morning rounds through the jail, walking through each hall and checking in with each of his guards before retreating to his office for the day to work on an endless stream of boring paperwork. He rarely ever went into the harshly lit hallways just for kicks, knowing that his presence made the prisoners more rowdy. There had been a few times when Castiel underestimated how alluring the prisoners found him, and each time he had walked around the halls just for the sake of walking, there was at least one man who tried to have his way with the attractive young warden. None of the prisoners had ever gotten farther than pushing him up against the wall before a guard appeared and the escorted the attacker to isolation for the evening.

Today he decided to start off with hall 6, wanting to ask Garth how the two new prisoners were doing. He had been briefed on the Winchester Brothers by his boss, Zachariah, and had skimmed over their files the night before. Both of the brothers seemed to have a lot of blood (speculated and certain) on their hands, and he quickly figured out that the younger brother, Sam,  was more of a background player while the older brother, Dean, was one to make sure his work was out in the open. Initially he had been shocked to see just how much the Winchesters had gotten away with, but had found himself intrigued with the photo of Dean, how his green eyes seemed to match the emerald stone which was set in the silver ring that Castiel wore on a chain around his neck. The ring had been his mothers, and when she had died he had taken it before his brother or sister could lay claim.

As he rounded the corner, he noticed that Garth was nowhere to be seen. He heard a low growl emit from the opposite end of the hall, followed by a grunt and then a crack. He ran to the cell just in time to see Garth’s unconscious body slide down the wall and slump over on the floor. His eyes flickered back to the other man in the room and his breath caught in his throat. Dean Winchester was nothing like the man in the photo. He was tall and strong, with a wider build, though not fat, his dirty blonde hair was cut short and somehow styled perfectly. His strong jawline was currently clenched and his lips were pressed tight together. Castiel looked Dean straight in the eyes and was momentarily distracted by just how green they were. They almost outshone the emerald in the ring, and Castiel cocked his head and narrowed his eyes when he noticed the panicked look held in those emerald eyes. How can this man, with fear written clearly all over his face, possibly be the murderer in those files? he wondered before tearing his eyes away from the prisoner and focusing his attention on the guard still hunched over on the ground.

He breezed past Dean and crouched down next to Garth, feeling for a pulse.

“Lucky for you,” he said standing up and turning back to Dean, “He’s only been knocked out. That was very stupid of you.”

“Yeah well what can I say?” the prisoner smirked, “Reckless is my middle name.” Castiel narrowed his eyes and reevaluated Dean; there was a drastic change in his demeanor, his lips were now curved into a greedy smirk and there was a coldness in his eyes that suddenly made it very easy for Castiel to see how this man could indeed murder.

“I said stupid, not reckless,” he corrected, “and I really don’t care what your middle name is.” Then he remembered the time and looked briefly around the room. Dean’s cellmate was absent. Breakfast time, he remembered. “Why aren’t you at breakfast?” he asked.

“Not hungry, but I bet you and I could think of a few things that might work up my appetite.” Dean grinned, winking at Castiel who felt a low heat burning the back of his neck as Dean’s emerald eyes raked over him from head to toe. He did his best pretending not to notice, but as soon as Dean took a step forward, he brought out his Taser, knowing that if Dean tried to overpower him, there were no guards anywhere near by that would be able to help Castiel. To Castiel’s relief, Dean froze.

“You should think carefully before taking another move,” Castiel warned. “I will not hesitate to use this, should a display of force be required.”

Dean’s smirk faltered as a look of recognition passed over his face. “You’re the warden.” He said, looking at Castiel in a new light.

“And you’re a murderer who just knocked out one of my guards because you didn’t want to go to breakfast,” he retorted.

Dean’s smirk returned and he glanced over at Garth before returning his gaze to Castiel and laughing, “Well, you should find better guards. It hardly took me any effort to take him down.”

True, Garth may not have been the best candidate physically for this position, but he had aced all the tests given and had majored in Psychology at college, which was why he had been assigned to this hall. He was one of the few guards who had been immune to all the mind games the prisoners liked to play, and he was the only one who was ever successfully able to reverse the games and make it so that the prisoners ended up with their head on backward.

“You never told me what your name is,” Dean said, his green eyes burning holes in Castiel’s head.

Castiel simply turned away from Dean towards Garth and quickly gathered him up and hung the guard over his shoulders. When he reached the door he turned back towards Dean and said, “My name is Castiel Novak. And unless you want to be tasered when I get back, I suggest that you go to the cafeteria and get some breakfast. Oh and Mr. Winchester, ” he paused to shift the dead weight of the unconscious guard, “the next time you knock out one of my guards, I will have no choice but to punish you and put you in isolation for a week.” With that, he left the cell completely and started down the hallway towards the infirmary. He heard Dean muttering something as he walked away but he didn’t try too hard to figure out what the man was saying.

A minute later, he was at the infirmary door, waiting patiently as the nurse, Naomi, scurried over to the door and opened it, helping Castiel move Garth to one of the beds.

“Cassie!” boomed a British voice from behind and Castiel turned to see Balthazar saunter into the room.

“Hello Balthazar. How are you?” Castiel asked politely; he rarely ever got to see his friend and it had been a long time since they last got to talk.

“I am doing wonderfully,” Balthazar grinned as he washed his hands and put on a pair of medical gloves, “This morning I had a ménage a- what’s the French word for twelve?” He winked at his friend, who responded by rolling his eyes and giving him an amused smile. Balthazar turned his attention to Garth and after some poking and prodding, turned again to Castiel, taking his gloves off and disposing them in the garbage can nearby. “Only a minor concussion and a sprained wrist I believe. He should be bright eyed and bushy tailed in a few days. As for now however, I should like to keep him here for the remainder of the day. To monitor his condition.”

Castiel glanced at Garth, noting for the first time the swelling of his right wrist, which was also turning an unfortunate shade of yellow. “Of course,” he replied, “just make sure to keep me updated on how he is doing, and see to it that he has a ride home for tonight.”

“Whatever you say boss.” Balthazar joked as he carefully pressed an ice-pack to Garth’s wrist.

Castiel said his goodbyes and made his way back to hall 6, walking down the silent corridor wondering if he would find Dean still standing there. He peered into the cell and found it empty.

Good, he thought as he made his way to the next corridor to check in with the guard stationed there. Maybe Mr. Winchester won’t be too much trouble after all.

Deep down he knew it was just wishful thinking.


	4. Chapter 4

**Notes for the Chapter:**

> In which we meet Gabriel and Crowley. #SabrielForever

“Heya kiddo, welcome to Perdition,” a man dressed in the official bright orange jumpsuit smirked as he sauntered up to where Sam was eating, a lollipop hanging loosely from his mouth, his eyes full of mischief.

“Perdition?” Sam said, tilting his head up slightly to get a better look at the man. He was a shorter guy with golden hair and eyes to match. He walked as if he were on top of the world and his confidence and trickster personality seemed to expand around him like wings, enveloping everywhere all at once. Sam noticed how a few of the other prisoners gave him bedroom eyes and Sam knew that nothing good could possibly come from knowing this man. Another short man, with dark hair, accompanied him;* he had sharp features, his lips spread in a coy smile, and Sam felt immediately on edge about him. He looked at how near the two men were standing to each other and it was obvious that they were close friends.

 _I wonder just how close_ , Sam mused, grimacing and shaking his head at the thought of the two men standing in front of him being lovers. He almost missed the other man’s response.

“Yes Perdition, you know moose, where the monsters get locked up.” The dark haired man chuckled, his eyes gleaming dangerously. Sam noticed the man had an English accent, but his attention remained on the man with the golden hair.

“Who said I’m a monster?” He asked, putting on his best wounded-puppy face and staring into the first man’s golden eyes. There was a beat of silence, and then the first man threw his head back and let out a long, loud genuine laugh that shook his whole body and sent little shivers down Sam’s spine. The dark haired man let out another little smile and rolled his eyes at his companion’s reaction.

“Name’s Gabriel Speight,” the golden haired man said, “but you can call me Gabe. This here is my partner in crime Fergus Crowley,” he said, slapping the rear of the man standing next to him who responded with a slight jump.

“You can call me Crowley,” Crowley griped, sending a scowl in Gabriel’s direction, which only succeeded in making the other man snicker as he turned back to Sam.

“So hotrod, I don’t think we have a name to put to that charming face of yours,” Gabriel said, cocking his head to the side and licking his lollipop suggestively.

“Sam. Sam Winchester,” he replied, pushing down the dirty thoughts that had begun to fill his mind as he watched Gabriel’s tongue flick and roll over the red lollipop.

Gabriel smirked and crossed over to Sam, plopping down in the seat next to him and throwing an arm over Sam’s shoulder. “What are you in here for? Let me guess, the jury decided that it was illegal to be so handsome so they threw you in here in hopes that this way you wouldn’t be able to corrupt their sons and daughters with that sinful face of yours.”

“Murder,” Sam said simply, “and credit card fraud and the illegal purchasing and selling of weapons, and a few other things.”

Gabriel pulled away for a moment, his golden eyes scanning Sam’s face in an attempt to figure out if he was being serious or not.

“I’m not lying,” Sam huffed, “my brother Dean and I screwed up and got caught. We had already been suspected of a couple other murders but the jury had never been able to convict us because they always lacked the evidence. I’d find the victim, Dean would torture and kill, then I’d clean up the place and make it impossible for anyone to get enough evidence to condemn us. But this time we just lost track of time and by the time we realized, it was too late.” Sam ran his fingers through his hair and sighed, leaning back against the table. Out of the corner of his eye, he saw Gabriel’s tongue dart out, licking his lips. He bit back a smirk. Good to know I’m not the only one interested. Then, just because he wanted to see the reaction of the shorter man, Sam closed his eyes and stretched his whole body slowly, his hands clasped above his head, his back arched slightly, his long legs sticking out straight in front of him. He heard a soft, sharp inhale next to him and chose to let out the dirtiest moan of pleasure he could, just loud enough for Gabe to hear, but not loud enough to have the entire prison try to jump him right there. He returned to a relaxed sitting position and scanned the rest of the room, his brown eyes never fully focusing on the other prisoners. He did his best to look bored as he let out another sigh and turned to the man sitting next to him. He counted it as a victory that Gabriel had moved slightly closer to him and that his eyes were now black with a rim of gold, his jaw hung slightly ajar and he seemed to have stopped breathing. Sam smirked. “Doin’ okay there Gabe? You look a bit dazed.”

Gabriel blushed slightly and then blinked and the look of pure desire was gone. His pupils were slowly returning to their normal size and the mischievous grin once again sat upon his lips. “I’m doin’ great Sammy boy. Just enjoying the view,” he teased, his eyes dramatically raking up and down Sam’s figure. Crowley let out a huff of annoyance and both Sam and Gabe jumped slightly at the reminder that they weren’t in private company. Then they both dissolved into a fit of laughter as Crowley took the seat on the other side of Gabriel.

“Yes, yes. Hilarious. You two really do know how to make an inmate feel like a third wheel.”

“No need for third wheels Fergie,” Gabriel snorted, “I’m all in for a three way, literally!” He winked at Sam and they both started howling in laughter as Crowley’s face took on a look of pure disgust.

“Not in this life time,” Crowley spat as he rolled his eyes at the childish behavior of the two men sitting on the bench next to him.

“So why are you two in here?” Sam asked a few minutes later, after the laughter had died down.

“We’re con-artists,” Gabriel said, as he tossed the lollipop stick to the ground. “Crowley and I run- well ran- a business called Just Desserts. It was a candy store that doubled as the most efficient way to get personal information.” He reached into his pocket and pulled out another lollipop, unwrapping it carefully and then popping it into his mouth. “Crowley here manned the front desk and would take down the credit card information. We rigged the scanner to not only make payment possible, it also took down all the information about the card and the owner. Card number, expiration date, home address. You name it. I would wander around the main floor with the little kiddo’s and chat them up, letting them try candies to see what they liked better. All the while, I’d ask them questions about their family, like if they were going on a vacation soon or if they were going to see dear old Grams and Gramps. The little brats were always so focused on the sweets, they’d tell me just about anything. After we got our information, we just had to play the waiting game. We were never suspected because the parents never knew that we knew when they were going to be gone. It was a good scheme until we hijacked a stolen credit card by mistake. The cops only figured things out after they went through all of our computer files and found our logbook of past scams.” Gabriel sighed and sucked thoughtfully on the lollipop, his eyes unfocused, staring blindly straight ahead of him.

“Why the hell did you keep a logbook?” Sam asked, surprised that they would have ever made such a stupid move. Every criminal knows you don’t record your victories in a way that could be read by anyone.

This time it was Crowley who replied. “We didn’t want to accidentally scam the same person twice in a row. We had the whole system set up where the program would catalog each of our scams and then when we received information about a possible scam, the program would cross check with our previous ones to make sure it had been at least five months and at least six visits since that last time we scammed that person. We didn’t know the police were going to get a warrant for our computer files so we didn’t think to delete them.”

“Thankfully we only got five more years left of our sentence,*” Gabriel said, coming suddenly back into reality. He turned and looked at Sam. “How long do you got?”

“Twenty years. No chance of early release for good behavior and no posting bail.” Sam sighed.

“Well shit. That really does suck Sam I Am.”

“Yeah, but I understand. I mean we killed a lot of people. Just because we could. They never really did anything wrong to us.”

“You know,” Crowley intervened, “twenty years doesn’t really seem like an appropriate sentence. I would have expected a lot longer.”

Sam looked over at Gabe who nodded in agreement with Crowley. “You’re right,” he said, turning back to Crowley, “at first I thought that no bail and no chance of early release was unreasonable, but thinking about what we did I guess that twenty years really is letting us off easy.”

The three prisoners sat on the bench talking as they finished their breakfast. They spent all day together and when it was time to go back to their cells, Gabriel grabbed Sam’s hand and kissed his knuckles playfully. Sam rolled his eyes at the gesture but something stirred inside of him and he found himself hoping that maybe one day that stupid con-artist would kiss him for real.


	5. Chapter 5

**Notes for the Chapter:**

> In which we meet Azazel and witness some more Destiel flirting. Also, Alastair is a douche. So is Lucifer.

Dean walked slowly to the cafeteria. He had been telling the warden and the guard the truth when he said he wasn’t hungry. He hadn’t been in a few days, but today had been the only day that Alastair didn’t personally escort Dean to breakfast, the first day he hadn’t been subjected to Alastair shoving prison food down his throat. On top of all that, Dean rarely ever got to see Sam. He heard the rumors about Sam and Lucifer, but he didn’t want to believe them. Apparently the younger Winchester and the head of the Italian Mafia had become fuck buddies within an hour of Sam’s arrival. Last night it seemed that Alastair and Lucifer were having a competition to see who could make their Winchester come first. The whole hall could hear the obscene slapping and slurping and moaning and panting and by the end, a few lonely, perverted ones had joined in. Dean had done his best to block out the sounds of his brother blissfully screaming out Lucifer’s name; just the sound alone had turned him off completely. To say Alastair was pissed would be an understatement.

Alastair had responded by immediately tightening Dean’s restraints and sucking a dark hickey right below his jaw, for everyone to see. Dean had only been able to screw his eyes shut and pretend that it wasn’t Alastair, it was… it was… Benny! Yes Benny, he would work. After all, Dean and his favorite fuck-buddy/bartender had enjoyed a night of erotic bondage when Dean had gone to The Roadhouse for a celebratory drink after killing that adulterous bitch Kate Milligan, and her bastard son Adam. They had fooled around before, but this night Dean had gone back with Benny to his apartment and had let himself be tied up, whipped, shocked, gagged, rimmed ruthlessly, and about a dozen other things that had him on the edge. For hours he laid there, shaking and panting, a broken mess, half sobbing for Benny to please just let him come. The bartender had just shushed him and spoken dirty nothings in his ridiculous southern drawl and even though Dean would deny it if he were asked, by the time the night was over and Benny had finally let him come, balls deep inside the bartender, hands still cuffed and gag still in place, he had fallen in love with the man. This being so, he high-tailed out of there as soon as he was able to walk properly, and hadn’t spoken to Benny since.

Yes, just pretend this is Benny. Relive that night, he told himself as Alastair started playing every trick in the book he knew. The whole thing ended up taking two hours, long after Sam and Lucifer were finished. It could have ended sooner except Alastair wanted to punish Dean for losing to his brother and Alastair’s boss. The minute Dean felt the cool metallic tip of the blade on his chest he had drawn in a sharp gasp, which was inhaled by Alastair’s greedy mouth. He had felt his cellmate's slimy tongue thrusting and exploring in his mouth and had hated every second of it. Then Alastair dug the tip of the knife into Dean’s collarbone and Dean had screamed in pain when Alastair shoved inside his dry, unprepared hole.

Dean paused at the door leading into the cafeteria and shuddered at the memory. Sucking in a deep breath he swung the doors open and strode over to the food. He stood straight and tall, his arms spread slightly out, enough to make him look bigger and tougher, but not so much that it looked weird. His face was set into a firm scowl and his cold eyes judged everyone he laid them on. His eyes locked with Alastair and he noted a look of impressed approval from his trainer. He had developed his mask over the years; he only wore it whenever he was dealing with something tough on the inside and with worthless people in reality. It was the same mask he developed when he was seven and he had to tell Bobby that he and Sam had bruises everywhere because they had been wrestling in the backyard and things had gotten rough instead of telling him that John had come home drunk and beat them both senseless. He had used it again when he was called into the principal’s office at the age of 11 and had told him that the reason he was failing his classes was because he didn’t really care about school instead of telling him that it was because he was too busy raising his little brother due to an alcoholic and abusive father who only ever came home to scream and beat up his sons and then sleep until he was sober enough to go get drunk again. He had also used the face this morning, when he tried to play macho instead of allowing himself to melt into those heavenly blue eyes that seemed to pierce through his bad-boy demeanor. He had never felt so naked and vulnerable than when Castiel was looking at him, studying him. As if he were drawing out all the little secrets that Dean never shared with anyone, not even Sammy, and had stored them away for a later time.

Dean grabbed his breakfast and made his way over to the table where Alastair and Lucifer were waiting for him. Curiously, Sam wasn’t there and Dean threw a curious glance at Lucifer who responded with a exasperated huff and an eye roll before turning to introduce the older man sitting next to him.

“Dean, meet Azazel. He’s one of mine,” Lucifer cooed, stroking the back of his hand down Azazel’s face. Azazel rolled his eyes and swatted the hand away, casting a heated glare at Lucifer who laughed quietly. “Azazel here is my inside hit man,” He continued, attention focusing back towards Dean.

“Hi,” Dean grunted, nodding at the man. Were it not for the harsh look in the man’s eyes, who were still fixed murderously on the back of Lucifer’s head, Dean would have never picked this guy out as a murderer. He reminded Dean of a camp counselor from a summer camp Dean had sent Sammy to one year when his father’s beatings had begun* to be more regular.

“Azazel, this is Dean. He will be taking over for Alastair and I when we get out.”

Suddenly Azazel’s attention snapped to Dean’s face and Dean felt slightly uncomfortable by the heavy gaze. “Not Dean Winchester?” Azazel smirked.

“Yes, how did you know?” Alastair spoke up, and Dean noticed a hint of worry in his voice.

“I knew his mama,” Azazel said, “Mary and I go way back.”

“Mary… Mary…” then a look of recognition passed over Lucifer’s face and Dean felt the hair on his arms rise. “Wait, not Mary Campbell?” Lucifer practically squealed with joy.

“What the hell! How do you know my mother,” he spat, pointing his finger accusingly at Azazel, “and how the fuck do you know her maiden name?” he said, turning on Lucifer.

“Dean,” Alastair warned and Dean realized that he was now clutching one of the plastic knives, waving it threateningly at Azazel. Dean let out a deep breath and tried to calm himself; he felt his fist relax and put the knife down carefully next to his untouched plate of food. Lucifer and Azazel exchanged amused glances, and then Azazel turned back to Dean with an evil smile on his face and a scary look in his eyes. He leaned in close and breathed into Dean’s ear.

“I’m the one who killed her.”

The next moment Dean found himself being hauled off of Azazel by three surly guards. He had leaped over the table and landed on top of the hit man, pinning him to the ground as he drove his fist again and again into the man’s face, screaming threats and cursing as each blow was successfully delivered. As the guards hauled him away he was slightly satisfied to see that Azazel was covered in blood and holding his nose gingerly.

“I’ll fucking kill you, you son of a bitch!” Dean hollered as he was dragged out the door. He heard Lucifer’s icy laugh and saw a look of pride mixed with fear cross Alistair's face. He stopped struggling as soon as the doors were closed behind him and let himself get led to a door on the opposite end of the prison. The nameplate read “Castiel Novak – Warden”.

Great, Dean thought, well at least this time it wasn't one of his guards.

The bigger of the guards knocked on the closed door, opening it when Dean heard Castiel’s voice from inside call out, “come in.”

“Ah, Uriel, Raphael, Zachariah, what do you need?” Castiel asked, head bent forward immersed in a tall stack of paper work, jotting something down before looking up. A surprised look passed over his face for a moment when his eyes landed on Dean. “Mr. Winchester,” he said, standing up with a sigh, “is there a specific reason you are not at breakfast?”

“We had to remove him,” Zachariah explained, “he decided that breakfast time is the perfect time to punch one of the other prisoner’s face in.”

Raphael muttered something about Dean being nothing more than a hairless ape and Uriel huffed in agreement, but they both quickly shut up when Castiel sent an icy scowl in their direction.

Sighing, Castiel turned to Dean and looked him over. “Thank you, you may return to your duties,” he said to the three men who nodded and filed out of the office, shutting the door behind them and leaving Dean alone with Castiel.

“Good morning Charlie,” Dean smirked and Castiel’s brow furrowed as his tilted his head.

“Excuse me?”

“You know, as in Charlie’s Angels?”

“I’m afraid I don’t understand that reference,*” Castiel said, looking thoroughly confused.

“C’mon man! Charlie’s Angels. With Diaz, Barrymore and Liu?” Castiel just pursed his lips looking more confused than before. “It’s a movie!” Dean huffed exasperated.

“Why is it pertinent?” the Warden asked, motioning for Dean to sit down.

“Really man? Uriel, Raphael, and Zachariah. Uriel and Raphael are angels in the Bible and Zachariah was visited by an angel! You’ve got your own little ‘Cassie’s Angels’ over here,” said Dean as he flopped into the chair offered and studied Castiel.

Castiel rolled his eyes and sat down across from Dean. They sat in silence for a few minutes before Castiel sighed and said, “Dean, you aren't going to be too much trouble for me are you?”

Dean was slightly taken aback by how informal the question was but he recovered quickly and smirked, “no promises, Trouble is my middle name after all.”

“I thought it was Reckless.” Castiel countered, a slight smirk on his face.

“And I thought you didn’t care.”

The warden rolled his eyes again and let out another sigh. “Within the past two hours you’ve knocked out one of my guards and attacked an inmate. Mr. Winchester, it’s as if you’re asking to be sent to solitary.”

Dean winked at Castiel and said, “Not necessarily solitary, but didn’t you mention something about needing to punish me if I stepped out of line?” Dean licked his lips and stared at Castiel’s chapped ones. He flickered his eyes back up to meet Castiel’s bright blue ones and was greeted with a slightly amused look. Suddenly Castiel was in his personal space and Dean could feel the warden’s warm breath against his ear.

“You want me to punish you?” Castiel whispered seductively and the gravely sound of his low voice went straight to Dean’s dick.  

“Yes sir,” Dean gulped as he squirmed in his seat; he felt Castiel’s hand grip his upper left arm and sucked in a breath when the warden released a breathy laugh which tickled Dean’s ear.

“Okay,” he purred and then just as quickly as he had intruded Dean’s space, he was gone. “For your punishment you can clean all the bathrooms. They must be completed by the end of the day.” Dean glared at Castiel who was trying hard not to smile at the very annoyed prisoner as he walked back to his side of the desk and sat back in his chair. He picked up his pen and resumed working on the large stack of papers.

Dean sat there stupidly for a few minutes before Castiel tore his eyes away from his work and looked at Dean. “You’re dismissed. Find Samandriel to get the supplies. He should be just three doors down.”

Dean nodded dumbly and walked out of the office, making his way to collect cleaning supplies from the man with the unfortunate name.

Dean got back to his cell around 11 pm and was greeted by Alastair crowding him up against the wall and sneering as he ripped Dean’s clothes off. Dean begrudgingly let himself be hauled over to the bed and tied down. Alastair was soon atop Dean thrusting into him unprepared, he nicked him with the knife as he scolded Dean for his outburst earlier. Dean was too tired to argue back so he closed his eyes and hoped that the pain would end soon.


	6. Chapter 6

**Notes for the Chapter:**

> In which I decided to make an entire chapter about the defining days in Sam and Dean's life that got them to where they are today instead of doing random back-story drops later on in places where they don't really make sense.
> 
> WARNING: John is a homophobic dickwad. Also Dean and Benny have the sex.
> 
> Enjoy!
> 
> For more Devil's Row tidbits, sneak-peaks and other Supernatural goodies, follow me on Instagram: @iamsmauglocked
> 
> A huge thank you to my darling BETA Meg for being the best editor in the Garrison.

_ November 2, 1983: _

_It was hot. Too hot. The heat circled and overcame Dean’s senses as he struggled to breath, the smoke becoming thicker in the air._

_“DEAN! Take your brother outside now! Run as fast as you can!”_

_John hurriedly handed Sam over to Dean who turned around and bolted down the stairs. He stumbled through the flaming debris, clutching his baby brother to his chest. The heat was suffocating and his throat was on fire from the smoke creeping in through his nose and mouth._

_“DADDY!” He screamed, but it came out as more of a hoarse whisper. Beads of sweat rolled off his face down his neck, he held Sammy even tighter. His eyes burned and he looked through the tears welling up, searching desperately for a way out. Finally locating a hole in the wall he ran as fast as he could. His feet hurt and he could feel fiery hot embers falling from above and burning through his thin pajama shirt. The panic built inside him and he made it outside seconds before hearing a loud creaking sound. A solid mass ran straight at him and hauled him up, carrying him quickly across the soft green grass and then across the street. John held his two sons as they sunk to the ground. Dean sobbed into his father’s shoulder as they watched their house burn down. A few minutes later Dean registered that the fire department was there, trying desperately to put out the flames that engulfed the only home Dean had ever known._

_“Dad?” he choked out once he had found his voice again._

_“Yes son?”_

_“Where’s mom?”_

_Tears streamed down John’s face as he turned his head away from Dean. Dean felt silent sobs shaking his father’s body and he threw his arms around him. Neither of them spoke, they only cried and clung to each other, keeping a now sleeping Sam tucked away safely between them. A few firemen walked over to them and told Dean that he needed to come with them so that they could make sure he was okay. Dean hiccuped and shook his head violently._

_“It’s okay son,” John told him, placing his hands gently on his shoulders and looking him straight in the eyes, “we need to make sure that you’re okay. They won’t do anything bad, I promise. I won’t let anything bad happen to you, ever.”_

_That was the day Sam and Dean Winchester became orphans._

 

 

 

_ January 24, 1989: _

_“Hey Daddy,”_

_“What Sam.”_

_“Well, I’m wonderin’ if maybe we could gets a cake?”_

_“Sam, we don’t need cake damn it! Don’t I already do enough for you? There is absolutely no reason for more junk food!”_

_“But Daddy…”_

_“I SAID NO DAMN IT! I’m going out! If you get hungry, I left some soup on the counter. Have Dean make it for you, I’ll be back later.” With that, John grabbed his jacket and the car keys and slammed the door. Sam heard the Impala starting up, followed by the screeching of the tires as John hurried away._

_Sam let out a sigh and waddled over to the kitchen. He looked around and pulled a chair up to the counter. Crawling atop it, he saw the cans of soup John had mentioned earlier as well as a loaf of bread. He made his way to the fridge and pulled out cheese and butter and then hauled them back to the counter. Once reaching the soup again, he pulled the lids off and carefully dumped the contents into an old pot that was resting on the stove. He set the cans back on the counter and opened the bread, grabbing four slices and stuffing cheese between them, coating the outside with butter. He set the two sandwiches on a pan and reached pudgy fingers out to turn on the stovetop. He hummed a Kansas song as he grabbed a wooden spoon and stirred the soup, waiting patiently until it was ready, flipping the grilled cheese until he was satisfied. He turned off the stove and crawled down from his chair, retrieving two bowls and two plates which he set on the counter. He carefully poured soup into the bowls and placed the slightly burnt grilled cheeses onto the plates. He got on top of the counter and opened one of the cabinets, reaching all the way to the back to where he knew Dean stored the candles. He placed ten of them in Dean’s grilled cheese and proudly carried the meal to the table, spilling half of the soup on the floor in the process. He quickly cleaned it up, then got out a lighter from Dean’s jacket and set it by his plate._

_He rushed over to Dean’s room and knocked on the door, “Dean? Dean I need to show you something!”_

_“What is it Sammy?” Dean said, opening the door and crouching beside the six year old._

_“C’mon!” Sam grabbed Dean’s hand and pulled him into the kitchen where the food was slowly getting cold. He dragged Dean over to his seat and then rushed to pull his chair up right next to his big brothers, smiling from ear to ear as he looked at his masterpiece. “Happy birfday Dean!” he screamed, throwing his hands into the air before jumping into Dean’s lap and hugging him as tight as his little arms could._

_Dean held his brother and stroked his shaggy hair gently; a tear escaped his eye and burned a trail down his face. He pressed a small kiss on the top of Sam’s head, “Thanks Sammy.” They pulled away and ate their food, Sam doing his very best to make Dean smile on his birthday and Dean faking happiness so that his brother wouldn't know how much it hurt him that John had forgotten that today his eldest son was turning ten._

_That was the day Dean Winchester realized that Sammy was the only family he had left._

 

 

_ December 25, 1995 _

_“Dean, he’s not coming,” Sam said, glancing from his homework to where Dean was pacing by the window. It had been two weeks since their father left and John had promised to be home for Christmas. It was now 10pm Christmas Day and they hadn't heard a word from him. Bobby had called, like he did every holiday since learning of their mother’s death._

_“He’ll be here,” Dean huffed, not looking his brother in the eye because deep down he knew that his father wouldn't be there. John had been leaving more and more and staying away longer._

_The first Christmas he missed he came home an hour before midnight, saying that he still “technically made it here on Christmas day boy! Don’t mouth off to me!” Sam had woken up from the sound of John and Dean arguing in the other room and had hidden behind his door when he saw John punch Dean square in the jaw. Dean fell to the ground, holding his cheek, tears streaming down his face. John huffed and replied with a “Man up son. You’re thirteen now! Time you grow up, and grown men don’t cry.” Then he stormed out and left Dean balled up on the floor, holding back tears. Sam crept out of his room and walked over to Dean, sitting quietly behind him and resting a hand on his shoulder._

_“It’s okay Dean,” he whispered, “You’re a much better man then he is.”_

_“Thanks Sammy,” Dean sniffed, “but Dad’s right. I do need to grow up. C’mon, time for bed.”_

_Now, for the first time in three years, Dean felt a tear slide down his cheek. He silently cursed as he swept it away with the palm of his hand. He cursed his father, and then cursed the Angels his mother once said were watching over him. Where were they the night she died? Where were they every time he and Sam fell victim to one of John’s drunken rages? Where were they when he had to suffer through his father missing another holiday or birthday?_

_That was the day Dean Winchester lost his faith._

 

 

_ June 13, 2000: _

_Sam finished his salad at the little diner a few blocks away from the hotel and packed up his school work. He glanced at his watch and realized that he finished his studying early today which meant more sleep._

_Maybe Dean and I can watch a movie, he thought as he tossed a few bills on the table for the waitress and walked to the front to pay his bill._

_Ten minutes later he was back at the motel; he slid the key into the lock and pushed the door open._

_“Oh! Oh GOD YES!”_

_“Mgnf, Dean! HARDER DEAN HARDER!”_

_“Benny, oh oh Benny,”_

_Sam froze in horror at the sight of his brother, straddling some guy, fisting him furiously as he drove himself into the stranger. They were both completely naked and covered in sweat and pre-cum. Eyes screwed tightly shut as they thrusted back and forwards in unison, moaning in pleasure. Sam cleared his throat and turned away. He heard Dean yelp and then a bang as he fell off the bed._

_“DAMMIT SAMMY!” Dean yelled, desperately trying to cover himself up. Benny looked utterly confused and Dean shoved a pillow onto the man’s crotch._

_“Is this your boyfriend?” Benny asked, with a noticeable southern drawl. He scanned Sam up and down before winking at the younger Winchester who grimaced back at him._

_“I’m his brother,” Sam said tonelessly._

_“Uh, Benny, I think you should leave,” Dean said, gathering up Benny’s clothes and motioning to the door._

_Benny sighed and turned to Dean, “Well, if you want to finish our little session,” he smirked, pulling his pants up and throwing on his t-shirt, “you know where to find me.”_

_A long shower and two beers later Dean and Sam sat across from each other at the small hotel room table._

_“Well, I guess the cat’s out of the bag now huh,” Dean sighed, taking a long sip from his beer._

_Sam looked curiously at him, “So… you’re gay?”_

_“Wha- no! I mean… not really,” Dean said, glancing down at his bottle, eyes fixing anywhere but Sam. “It’s just that… uh… well honestly it’s like this. When it comes to guys versus girls, I don’t really care. In the end, I’m kinda just attracted to both ya know. I like who I like and sometimes it’s guys and sometimes it’s girls.” His head suddenly snapped up and he looked Sam straight in the eye, “you can’t tell Dad,” he whispered, and Sam could hear the fear in his voice. “Whatever you do, just don’t tell Dad.”_

_“Don’t worry Dean, I won’t. I can kinda relate to what you’re going through actually,” Sam blushed a little and looked down at his hands and said, “I’ve only ever liked guys.”_

_There was silence for a minute then Sam felt a hand on his shoulder and looked up at his brother who had a proud, yet sad smile on his lips. “Your secret’s safe with me.”_

_That was the day when Sam and Dean Winchester finally got to be true to themselves._

 

 

_ August 28, 2000: _

_“RUFUS JUST TOLD ME THAT I HAVE FUCKING FAGGOTS FOR SONS!” John Winchester raged, slamming through the door in a drunken mess, throwing everything he could lay his hands on. Dean raced out of the kitchen where he had been cleaning up after dinner._

_“Dad, please, you have to be quiet. Sam’s asleep and he’s got a big test tomorrow and-”_

_“SHUT UP!” John roared, slapping Dean across the face so hard the force made him fly to the floor. There was a sickening crack as Dean’s skull made contact with the cold cement floor._

_Suddenly, John was on top of him, throwing punches anywhere his drunken hands could reach, his boozed up brain having only one mission: to beat the gay out of his son. Dean’s head felt heavy and there was a loud buzzing, the edges of his vision were going dark and he could feel a trickle of blood seeping out of the back of his head. He was vaguely aware that he was crying and as he slipped in and out of consciousness he could hear his father yelling at him from somewhere far away._

_“REAL! *punch*MEN! *punch* DON’T! *punch* CRY! *punch* FAGGOT!!*punch*”_

_Then something was added to the noise, the sound of heavy footsteps running down the stairs and Sam’s voice yelling for John to stop. Suddenly John’s weight was gone and Dean watched in horror through heavy lids as their drunken father turned on Sam._

_“You,” he hissed, the hatred clear in his otherwise drunken voice. “You disappointment!” He lunged at Sam and slammed his fist full force into Sam’s gut. Sam’s eyes went wide and then his whole body seemed to crumple._

_“No,” Dean moaned, forcing himself to stay awake. He crawled over to the coffee table and struggled to stand up, then he took off to the kitchen as fast as he could, hoping to reach the phone and call the police, Bobby, someone. He made it to the sink when he heard John’s footsteps racing up behind him, grabbing the first thing he could to use as a weapon, he whirled around to protect himself from the man who was supposed to love him unconditionally. He felt the blade sink into John’s stomach before he registered what was happening. His hand was quickly covered in thick warm blood as it rushed out of the wound and spilled out onto the white linoleum floor. John’s eyes widened and he clutched Dean’s shoulder as they both sunk to the ground._

_“Dean,” he murmured, his eyes slowly closing and his face growing pale, “take care… take care of Sammy.”_

_“Yes sir,” Dean said. John let out a final breath and Dean watched the lights go out of his father’s eyes. He sat there, clutching his father’s corpse, crying for his death. Crying for the death of his mother, crying for the treatment he and Sam had to endure these past sixteen years. Finally letting free all the tears he had kept locked away. That’s how Sam found him half an hour later; sitting in a pool of John’s blood, holding onto his body for dear life and crying his heart out._

_“Dean,” Sam gasped as he rushed over to his brother. He threw his arms around Dean’s neck just like they did when they were kids and together they cried. Sitting in the pool of blood until it turned cold and started drying, holding onto each other, afraid that if they let go, they would lose each other for good._

_That was the day Dean Winchester became a murderer._


	7. Chapter 7

**Notes for the Chapter:**

> In which Sam is in love with Gabriel, but Lucifer is Satan. Dean is a bit tied up at the moment, but he might have a plan.

It had been three months since their arrival at Folsom Prison and Sam saw less and less of Dean as the weeks went by. It seemed that his older brother was always in some sort of trouble, between punching a guard to knocking out an inmate, Sam was starting to worry. To make matters worse, Lucifer seemed to be enjoying Dean’s constant punishments and Sam had caught him encouraging Dean to fight back whenever someone told him he was wrong. The only good thing that was coming out of this mess was that since Lucifer and Alastair were concentrating mainly on Dean throughout the day, Sam was free to hang out with Gabriel and Crowley.

Sam and Gabe had bonded quickly and Sam learned that Gabriel and Crowley had met when Crowley married Gabe’s sister, Hester. Hester had been a kindergarten teacher and had used the classroom to get information about the students that Gabe and Crowley later got via Just Desserts. Crowley’s son Gavin was in Hester’s class, and when their trip to Abbadon’s Forest was cancelled last minute, Hester was caught red handed trying to rob them blind. Sam didn’t understand how that sparked a relationship, but Gabriel explained that Crowley agreed not to press charges if Hester would go on a date with him. Three months later they drove down to Las Vegas for a shotgun wedding and stayed happily married for the next six years until a woman named Megan stabbed Hester during a get-away gone wrong. After that Crowley hunted Megan down, eventually chasing her near an abandoned warehouse where he slit her throat and left her here alone to die. When he returned he told Gabriel that he wished to continue in Hester’s memory, and thus Just Desserts was opened.

Every day there was a new story; the three men took turns, Gabriel and Crowley often adding on to each other’s stories, and every day Sam found himself wanting to know more and more about them. Specifically about Gabriel Speight, whose eyes lit up every time he found a story interesting, his attention fully focused on Sam and a ridiculous lollipop always rested in his mouth. Whenever Sam locked eyes with Gabriel’s golden ones, he had the urge to close the distance between them, pull the candy out of the trickster’s mouth and replace it with his tongue; he wanted to taste the sugar, to press their lips together and hold him close while running his fingers through Gabe’s long messy golden hair. He wanted to feel the stupidly beautiful con-artist all over him, to claim him as his own. Whenever Gabriel noticed how Sam’s pupils were dilated and that he had seemed to stop breathing and was leaning slightly forward, he would smirk and pull out his sucker with a pop, then proceed to lick his lips and wink before bringing the lollipop back to his mouth and sucking away happily on it. Crowley would roll his eyes and mutter something that neither Sam nor Gabe would pay any attention to, and that was how they’d spend their days.

Every night when Sam got back to his cell, Lucifer would be waiting. Sam didn’t have a problem with what he and Lucifer were doing, even though sometimes he wished it were Gabriel sinking into him and making him sweat and moan into the sheets, turning him into a writhing mess, pounding hard enough to make him feel it the next day. But tonight was different. Tonight when he got back to the cell Lucifer wasn’t anywhere to be seen. He got ready for bed and crawled under the scratchy blankets when he heard the cell door creak open then clink shut. Suddenly, Lucifer pulled Sam out of bed by his hair and shoved him against the wall.

“You think he loves you?” Lucifer hissed, nipping hard at Sam’s ear and drawing blood. “Sammy, are you really that stupid? He’s a con-artist for fucks sake! He’s playing you and you are too dumb to even realize.”

“What are you talking about,” Sam gasped as Lucifer pushed his leg in between Sam’s thighs and started rubbing it against the younger Winchester’s crotch. “There- there isn’t anything going on between Gabe and I.”

“I know,” Lucifer sneered, licking the blood, “but I also know that you want there to be.”

Sam let out a suppressed moan as his cellmate sucked a dark bruise into his neck, biting it hard and then kissing the tender skin. “I- I don’t know what you’re talking about,” Sam whispered, “Gabe is just another prisoner.”

“LIES! I can see the way you look at him Sammy, I know that you long for his touch. Even when I’m inside of you I can tell that there are times you wish he was the one pushing you over the edge. But remember, you’re stuck in the pit with me, I run the show. This is the deal you made and you can’t shut me out, no matter how much you think you want to,” he snarled, throwing Sam to the bed and then carefully crawling on top of him. Lucifer lay there, gently running his fingers through Sam’s hair and starting into his eyes. Slowly he started grinding and smirked when Sam moaned again. “Thing is Sammy, the only reason Gabriel is even talking to you is because he knows that you’re mine. He thinks that if he can take you from me, it will mean that he is the top-dog around here. He doesn’t really want you. He doesn’t really care about you. He’s just doing what he does best, he’s coning you.” He stroked Sam’s face and cupped his jaw, planting a loving kiss on Sam’s lips. “I want you Sam. Hell, I need you. When that idiot warden, Novak, told me I was getting a new cellmate, well to be honest, I hated the idea. But then you walked in and I knew that something good was going to happen. I knew that you were the true one for me. From the beginning of time, it’s always been you Sammy.”

Sam closed his eyes and let himself melt into the warm body strewn atop his own, he felt Lucifer’s lips meet his again and this time he brought his hands up to grab the back of Lucifer’s neck, pulling him closer as their tongues tangled together, tasting, searching, claiming their territory. In the back of Sam’s mind, something warned him against continuing with Lucifer, but he pushed the thought so far down, not even an Angel could raise it. Grabbing Lucifer’s torso, he flipped them both over so that he was on top. Lucifer pulled away for a moment, surprised at Sam’s sudden need for control;* he had always been content with being the bottom and this was the first time Sam had shown any form of dominance. The look of shock was quickly replaced with that of unadulterated lust and soon their mouths found each other again, their bodies tangled together in a mass of needy limbs, hands wanting to be everywhere at once. Eventually they were both naked, Sam thrusting deep into Lucifer, jacking the mafia boss off in time to each of his thrusts. They were both moaning and panting, like animals in heat and then Lucifer arched his back and howled Sam’s name as he reached his high, Sam followed suit soon after, burying his face in the crook of his cellmate’s neck and screaming his name as he thrusted as far as he could one last time, coming deep in Lucifer’s ass.

They lay there for a time, listening to each other’s breathing slow down, their pounding heartbeats growing quieter. After a while Sam realized that he was still buried inside Lucifer and slowly pulled out, drawing out a low moan from both of them. Sam rolled off of Lucifer and lay with his back facing the wall, turned towards Lucifer who in return, draped a leg over Sam’s hips and pulled him close. Sam closed his eyes and relaxed into Lucifer’s touch. He started humming a song Sam wasn’t familiar with and soon they both fell into a peaceful sleep.

Then next morning Sam awoke not knowing which limbs belonged to him, and which were Lucifer’s. He lay in silence for a few minutes, watching his cellmate sleep, and then he let out a sleepy groan and disentangled his body from the sleeping Mafia boss’. He was brushing his teeth when he felt warm hands gently grab his hips and a firm body press into him from behind. He smirked when he felt Lucifer prop his chin on Sam’s shoulder and mutter a sleepy, “mornin’ Sammy,” before his waist was being circled by two strong arms. The two men stood there swaying slowly while Sam finished brushing his teeth. When he was done, he turned around in Lucifer’s arms and planted a small kiss on his forehead.

“You should get ready for breakfast,” Sam murmured, wrapping his long arms around Lucifer’s shoulders, pulling him in closer.

Lucifer looked up at him curiously, “will you sit with me today?”

Sam immediately saw Gabriel’s golden eyes and imagined the hurt look the con-artist was sure to have when Sam didn’t come find him, but then he remembered what Lucifer had said about Gabriel only wanting him because he was Lucifer’s. While Sam didn’t particularly enjoy being anyone’s “property” he sure as hell didn’t want anyone only wanting him because he was someone else’s.

“Of course I’ll sit with you,” he said, his eyes meeting Lucifer’s, “actually, I think I’d like to make it a regular occurrence.”

Lucifer seemed to radiate with happiness and Sam saw a slightly worrying gleam in the other man’s eye. He wasn’t able to focus too much on it however before he was being dragged out of the cell towards breakfast, hands locked with Lucifer’s as they walked down the hall.

When they had gotten their food and reached the table, Lucifer introduced Sam to Azazel and two other men named Roger and Dr. Green, who were affectionately referred to as War and Pestilence. He nodded a greeting at the three men.

“Where’s Dean?” he asked, turning to Alastair.

“Dean is a bit tied up at the moment,” Alastair snorted, smirking slightly as the other men at the table chuckled darkly. Sam tried not to look too worried as he took a bite of his toast but he couldn’t help let out a sigh of relief when a few minutes later he saw Dean enter the cafeteria.

Dean looked like he had been to hell and back. His face was unshaven and he had dark bags under his eyes. Sam quickly noticed that his older brother was limping and that his neck was covered in dark purple hickeys. Their eyes met for a moment before Dean broke into a wide smile, Sam got up from the table just as Dean set down his food and the two brothers reunited with a long hug. Sam felt some of the tension leave Dean’s shoulders as he mumbled, “good to see ya Sammy.”

“You too Dean,” Sam replied, pulling away and studying Dean’s face. Dean looked different, much different. When they arrived Dean had just been a cocky murderer, now he was a tortured soul and Sam was angry with himself for not making an effort to see his brother before now. They sat down next to each other and listened to the conversation happening around them, neither saying another word. Sam noticed that when Azazel spoke, Dean’s body went rigid and he glared at his food as if it had personally offended him. Sam was curious, but he knew better than to ask Dean in front of everyone else.

“Wanna take a walk?” He asked, looking over at Dean and loading everything in a pile on his tray.

Dean looked relieved and quickly did the same, “sure.”

They put their trays and dishes in the designated areas and made their way to the courtyard, both staying silent until they were sure that no one could hear them. They found a tree at the edge of the property and sat under it.

“So…” Sam started, and at the same time Dean said,

“Fucking Azazel killed our mom.”

Sam stared at him for a minute, then leapt up with a fire in his eyes and started marching back towards the dining room.

“DAMMIT SAMMY!” Dean cursed, running after him and blocking Sam’s path.

“Get out of my way Dean,” he growled.

“I already beat him up Sammy, it didn’t get me anywhere other than cleaning the bathrooms and…”

“And what?”

“Never mind, the point is, you can’t do anything to him without getting in massive amounts of trouble.” Dean sighed and ran his fingers along his scalp, “C’mon Sammy, you gotta trust me on this one. Just let it be for now. We can figure out something later.”

Sam frowned and looked Dean over again, something was very wrong. Three months ago, Dean would have been all for killing the son of a bitch who killed their mom. Now, he just stood there dejectedly.

“What the hell did Alastair do to you?” Sam asked, true concern written clearly on his face. Dean let out another long sigh and turned away from his little brother.

“Trust me, you don’t want to know.”

Sam hesitantly followed Dean back to the tree and they both sat down again, Dean covered his face in his hands and Sam hesitantly put an arm around his brother’s shoulder.

“Dean,” he started, “Dean, please, you can talk to me. What’s going on?”

They sat under the tree all day, Dean told Sam about Alastair and what he was making Dean do. How in the past week alone Alastair had made him beat up a guard and two other prisoners, for no reason other than to prove that he could do it. How because of this, he was sent to the warden’s office where he received punishment for violence. He talked about Castiel, how his eyes were the bluest blue he’d ever seen, how he always had ridiculous sex hair, the dark brown color making his eyes even bluer. He told Sam about his punishments, cleaning the bathrooms, weeding the front garden, cleaning the dishes, once he had been sent to the basement to catch the rats. Each time he was punished he’d get back to the cell after curfew and Alastair would be waiting, knife in hand, ready to punish Dean for being late. He showed Sam some of the scars from where Alastair carved into him while he forced himself in Dean. He told Sam about how Azazel was the one who killed their mother; how he wasn’t even sorry that he’s done it. Dean finally told Sam that last night Lucifer and Alastair had tied him to the bed and taken turns cutting him while giving him his final task before he was deemed ready to take their place when they busted out. He had to rape Castiel. Had to own him, claim him, make Castiel beg for both sexual release and release from bondage. He cursed the tear that fell from his eye and splashed into his lap as he recounted the events of the past three months. Sam sat quietly and listened rubbing Dean’s back and when Dean finished his story Sam pulled him into a hug and started humming the lullaby their mother used to sing to Dean.

When Dean settled down he turned his teary eyes to Sam and let out a small smile, “So Sammy, enough about me. What’s new with you?”

Sam told him about Gabriel and Crowley and their crazy adventures. Dean smiled when he noticed the faraway look in Sam’s eyes as he talked about Gabriel and his obsession for sweets and his passion for tricks. Then Sam told him about Lucifer, told him everything. The things he and Lucifer did in the night, he told Dean what Lucifer had said about Gabriel only wanting Sam because he was Lucifer’s and everyone knew it.

“You don’t belong to anyone,” Dean spat in disgust.

“I know that, but from the outside it looks like I do. I mean, think about it Dean. We arrived three months ago and by the end of the day Lucifer and I were already fucking. It’s not like I’ve been fighting it,” Sam countered, drawing a symbol into the dirt at the base of the tree.

“Do you want to? Fight it I mean. Do you want to get out?”

Sam looked up, Dean’s bright green eyes pierced through his defenses and he slowly nodded his head.

“Then we will. I have a plan.”


	8. Chapter 8

**Notes for the Chapter:**

> Oh look. Pain. 
> 
> ehehehehe you are all going to hate me.
> 
> #SorryNotSorry
> 
> Enjoy the update beyotches!
> 
>  
> 
> BTW: I am on Omegle Video right now if any of you want to chat! Type "IAmSmaugLocked" and "Devil's Row" in the interest box! If you find me I'll give you spoilers for the next chapter!!

Gabriel and Crowley sat on their bench, eating in silence. Neither had heard from Sam in two weeks and every time Gabriel tried to talk with him, he was blocked out by Lucifer’s posse. Once he even tried to visit Sam in his cell only to get five feet away from the door and hear Sam and Lucifer’s lust filled activities loud and clear. He knew he’d never be able to get the sound of Sam’s moan out of his head, but unfortunately it was corrupted with the sounds of Lucifer’s moans, and the sound of the mafia boss’s skin slapping against Sam’s had made Gabriel haul ass back to the infirmary where he threw up everything in his stomach and was admitted for the rest of the day. After that he stayed his distance. Clearly Sam didn’t want him like he thought Sam had, and he couldn’t bear to hold onto the idea of what if.

To get the thoughts of Sam out of his mind, he had started flirting with the prison’s doctor, Dr. Roche, who everyone just called Balthazar. At first Balthazar had been kind of a dick, but after an hour of watching Gabriel’s moping in the infirmary, clearly absorbed in self-pity, Balthazar had decided to ask the strangely handsome prisoner what was wrong.

“Guy issues,*” Gabriel mumbled.

“I’m a guy, at least I was last I checked.” Then Balthazar proceeded to look down his pants and nod, “yup, it’s still there,” he said looking back up at Gabriel, “no worries, it seems I am still a guy.”

Gabriel had stared at the doctor for a moment before he threw his head back in laughter. He spent the rest of the day there, talking with Balthazar, who he quickly nicknamed “Balthy” (which the doctor hated). The next day, Gabe went back to the infirmary and the two men talked whenever Balthazar didn’t have any patients.

Balthazar wasn’t Sammy, but he made a decent distraction. And that was all Gabriel really needed; a distraction.

Gabe’s mind was snapped back to the present day when he felt the palm of someone’s hand strike his face. He moved immediately ramming his fist into the bag of dicks who was behind the assault. He heard a pained grunt and then yelped when his arm was twisted behind his back and he was slammed onto the table. He struggled against the weight pinning him in place.

“Are you Gabriel Speight?” a voice growled next to his ear, the hot breath rustling his hair slightly.

“Who wants to know?” he countered, receiving a cuff to the back of his head.

“Answer the damn question.”

Gabriel tried once more to turn around and look at his attacker, but it was no use. Where the fuck was Crowley?

“Fergie? A little help please,” he grimaced.

“You mean the British guy? He’s a bit out of it right now. I may have slipped something into his tea.” Gabriel could hear the smirk in the stranger’s voice and he rolled his eyes. “You didn’t answer my question, are you or are you not Gabriel Speight?”

“I am.”

With that, the stranger let go of Gabriel, who whipped around to take a look at the other prisoner. He was handsome, with bright green eyes and sandy brown/blonde hair, pouty lips and light freckles dusting his stern face.

“I’m Dean, Dean Winchester. Sam’s older brother. I believe you’re a friend of his.”

Winchester? Dean? Sam’s brother? What the hell does he want?

“Well, I wanted to talk to you about Sammy,” Dean said, and Gabriel blushed slightly when he realized that he said the last part aloud. He looked over and noticed Crowley, passed out next to him.

“What about him?” Gabriel asked harshly, keeping his eyes carefully averted from Dean’s.

“He’s in trouble.”

Gabriel snapped his head forward and glared at the elder Winchester, searching frantically for the tiniest hope that it was a lie. He found nothing but pain and concern on Dean’s face. For the first time he noticed the hollow look in the green eyes and how the dark bags aged the man. Dean’s concern was genuine.

“What do you mean?”

“It’s Lucifer, apparently Sam jumped into something without thinking first, no pun intended,” he grimaced before continuing, “and now he’s screwed.” Gabe shot his eyebrow up which earned a huff from Dean who said, "again, no pun intended.”

“Are you sure Sam doesn’t want this? Because I went to find him the other day at his cell to try and figure out what the heck was going on and he sure sounded like he was enjoying his arrangement with Lucifer.” The memory made Gabriel shiver and he pushed it as far back into his mind as he could. “Anyways why should I care?”

“Because you love him,” Dean stated. Gabe glared at the audacity of the assumption before bowing his head and letting out a deep sigh.

“You know what Chucklehead, I think I just might. What do you need me to do?”

\-----

Four days later Sam woke to Lucifer cupping his balls and mouthing at his thighs. He let out a low groan when he felt the slick warmth of Lucifer’s tongue sweep up his length along the vein leaving a trail of saliva behind; Sam shuddered when his cellmate winked at him and then blew softly back down his length, the wetness from his tongue cooling drastically.

“L-Lucifer, please,” Sam started, wanting Lucifer to stop, but his thoughts were interrupted when Lucifer suddenly took him into his mouth. Sam had learned long ago that his cellmate no longer had gag reflexes, but that didn’t stop him from crying out every time Lucifer deep-throated him and swallowed him down. The muscles in Lucifer’s throat drawing out gasps and moans from Sam. Sam entwined his fingers in Lucifer’s hair and yanked him closer; he realized that his hips had begun thrusting of their own accord and deep down he hated himself for the way his body was reacting to this. He really wanted to end things with Lucifer, but how could he when he lived with the man. When he woke up every morning to Lucifer right beside him, once he woke up to Lucifer inside him and there had been several times when he woke up to find Lucifer naked, riding on his half limp cock like there was no tomorrow.

Sam cursed when Lucifer stuck his fingers in Sam’s mouth, but he sucked diligently, knowing it was better to go along with whatever Lucifer wanted than it was to deny him. Sam knew that if he told Lucifer no, the Mafia Boss would back off. It was clear to everyone that Pellegrino had it soft for the younger Winchester, but Sam also knew that saying no would make Lucifer even more horny later, and it was usually after being denied when Lucifer was the roughest. Lucifer pulled his fingers out of Sam’s mouth and Sam let out a gasp when he felt one of the long digits enter his hole.

“Still a little loose from last night I see,” Lucifer smirked, pulling off Sam’s cock and planting a tender kiss to its head.

Sam moaned as Lucifer added another finger and gently began scissoring him wider, then a third finger was added and Sam was squirming beneath his cell mate, begging for more.

Then Lucifer pulled out, stood up and walked out the cell door calling, “C’mon Sammy! Everyone is waiting for us at breakfast!”

Sam lay on the bed shaking, nerves on fire, gasping in short breaths trying to calm down. He jerked himself off and then cleaned himself up before putting his clothes back on and slowly making his way to the cafeteria. His legs felt like jelly and his mind was mush. That was the fourth time this week Lucifer had woken him up like that, and it was driving Sam crazy.

To top it all off, Lucifer kept making cryptic comments about Alastair and Dean and how soon it would be time for Dean to show them what he was made of. Dean would shudder and stare blankly at his food for a while before earning a thwack on the back of his head from Alastair who would hiss something about Dean needing to stay strong for certain performances he was being required to do. It took all of Sam’s self-control to not throw up at the thought of Alastair raping his brother. Dean had once been so confident and cocky, and whenever Alastair and Lucifer and their gang weren’t around, the old Dean came back, but as long as they were around, Dean had been reduced to a seemingly useless sack of bones. Sam knew that those bones still carried a soul.

The more Alastair and Lucifer tortured Dean, the worse his attitude and temper became. He was now getting hauled to Castiel’s office every day and had cleaned basically every room in the prison. Sam knew that Dean secretly didn’t mind the excuse to getting to see the Warden though. For whatever reason, Dean had latched onto the idea that Castiel Novak was his personal angel. In a way Sam had to agree. It seemed as if the warden was less harsh on the older Winchester and only wrote Dean up whenever a guard was seriously injured. Castiel had also started to monitor their hall, focusing most of his attention on Dean’s side which pissed Alastair off to no end. Afraid of getting in trouble for having a weapon, Alastair quickly passed the shank on to Lucifer who kept it on his person at all times. This meant that Alastair had to get creative when torturing Dean and judging by the fingertip sized bruises scattered among the hickeys on his neck, Alastair was doing a good job.

Sam sat at the table in between Lucifer and Alastair, he scanned the cafeteria for his brother but noticing the smug look on Alastair’s face he quickly realized that Dean was probably tied up in his cell, waiting for a guard to find him. Breakfast passed the same as usual, with the mafia members bantering crudely and Lucifer draping his arm over Sam, publicly sucking the occasional hickey onto his neck or shoving his tongue down Sam’s throat. When breakfast was finished, the group walked outside to their corner of the courtyard and Lucifer pulled Sam onto the ground and leaned against the younger Winchester’s firm chest, smiling smugly at any prisoner who glanced their way. The guard on duty, Cain, was one of Lucifer’s inside men and so he didn’t pay any attention to the group, other than to walk over and give Lucifer and Alastair a report on what was happening behind the scenes.

Sam absentmindedly looked around for Gabriel and Crowley. He knew that Gabe was just trying to con him; he knew that the little trickster didn’t really love him but he couldn’t help himself. He had been able to stay away from him and Crowley for the past two weeks and he wasn’t about to disappoint Lucifer just because he had a crush. He let out a small sigh when he didn’t see either of the con-artists and directed his attention back to his current group.

“You must have tied him up well Alastair,” Azazel smiled, pulling a cigarette from his pocket and carefully unrolling it. “He’s never had to miss breakfast before. Just how rough were you with him last night?” He laughed, dumping the unrolled tobacco into his hand and bringing it to his mouth to chew.

“Sorry Azazel, I don’t fuck and tell,” Alastair smirked throwing a wink at Sam who cringed and looked away.

“Azazel, be nice,” Lucifer laughed, reaching back and entwining his fingers in Sam’s hair and pulling him down for a kiss. Sam screwed his eyes shut and waited for it to be over, he wrapped his arms around Lucifer and pulled him closer so as to keep up appearances. Lucifer let out a small moan and ground his hips back into Sam’s.

“Oh God, get a cell,” War groaned, rolling his eyes. Pestilence snorted in agreement and they both received a heated glare from Alastair.

“Back away from my brother you jackass.”

Lucifer pulled away from Sam slowly and turned towards the voice. Standing a few feet away was Dean, a bright purple bruise covered his right eye and his fists were clamped tight at his side. Behind him stood Gabriel, scowling darkly, eyes trained on Lucifer. Sam felt Lucifer tense before getting up and walking over to face Dean and Gabriel. Crowley walked up behind Gabe and looked over at Sam, casting him a pained smile before glancing around at Lucifer’s group who were now making their way to support their boss should a fight ensue. Azazel growled and spat his chewed tobacco in Dean's direction. 

“Dean, think carefully about what you’re doing,” Alastair hissed, “you know better than anyone what we are capable of.”

“Do you really think I fucking care?” Dean growled. “You fuck me day in and day out, I never get a break but I take it and I don’t say anything about it because apparently I was chosen to take your place or whatever. But here’s the thing,” he advanced on Lucifer, “you told me once that when I took over for you, my family would come first and foremost, and those under your control would be considered my family. Well how am I supposed to support those dicks when I don’t do anything to protect my real flesh and blood.”

“So what Dean, you call in con-artists to help you on this failed mission? Dear Sammy is mine, not Gabriel’s and not yours. He said yes to me when he first got here, I gave him a way out. Hell I’ve given him many opportunities to change his mind. I kept my mouth shut when he went roaming around with this little slut didn’t I?” Lucifer said, pointing at Gabriel who sneered and took a threatening step forward only to find himself being held back by Crowley.

“Lucifer you great big bag of dicks, if you touch another hair on Sam’s head I will make sure that you die a hundred deaths,” Gabriel spat, lunging once more for Lucifer and again being held back by Crowley. He cast a dark look at his partner before turning a much softer gaze to Sam. 

"Why do you care?" Sam spat at Gabriel, "you were just using me to get ahead in prison."

"What are you talking about Moose?" Gabe asked, looking genuinely hurt at such an accusation.

"Lucifer told me all about your little con! Pretending to fall in love with me so that you could steal me away from the Mafia Boss and earn the ranking of top dog."

"Look, I may be a top, but falling in love with you wasn't a trick, I really did fall for you! Why is that so difficult to believe?"

"Y-you fell in love with me?"

“Enough with the chick flick moments! Sammy, get up. Let’s go,” Dean snapped, holding out a hand to his little brother and glaring at Lucifer and his posse.

“Gabriel doesn’t love you,” Lucifer whispered in Sam’s ear, causing the younger Winchester to freeze and look Gabriel in the eyes. “He’s playing you remember. And it seems that he’s got Dean in on it too. Don’t worry though love, I’ll take care of everything.” And with that, Lucifer reared around and whipped out the shank, thrusting it deep into Gabriel’s stomach.


	9. Chapter 9

**Summary for the Chapter:**

> In which Dean is sent to isolation for reasons.

**Notes for the Chapter:**

> Hey everyone! I'm back!! Sorry about the mini hiatus, I went to my grandfathers house and didn't have internet so there was no way to send in the next chapter for editing. Thankfully my lovely beta Megan got back to me very quickly (everyone thank her immensely!) and now we have Chapter Nine! Whoop whoop! Chapter 10 will be posted soonish and I think you are all going to enjoy it very much. It is one of my favorites.

“GABE!” Sam shrieked, watching as Gabriel sank to the ground. Crowley caught him just before he hit the cold hard dirt; he too was yelling something but Sam could only hear the words coming out of his brother’s mouth.

“YOU FUCKING BASTARD! YOU WANT ME TO PROVE MYSELF? WELL HOW IS THIS FOR PROOF?”

Sam watched as Dean leapt over to Alastair and in one quick motion, snapped his head. Alastair dropped like a puppet cut loose from its strings and Lucifer howled in anger. The Mafia Boss waved his bloody weapon at Dean threateningly and then lunged. Dean jumped out of the way and quickly pinned Lucifer’s arm to his back, knocking the shank from his hands. He threw Lucifer forward and retrieved the knife. Then he started his advance on Sam’s cell mate. Lucifer was doing his best to hide the fear in his eyes, but Sam saw it clear as day.

“You may kill me Dean Winchester, if you think it will bring you closure. But know this, a Mafia Boss gets to make one final rule before his departure, and it is his last wish that every Mafia member has to abide by no matter what. My final rule is this; you have twenty-four hours after killing me to make the Warden your little bitch. Fail, and both you and your brother will be killed, succeed and take my place as Leader of the Italian Mafia.”

“Bite me,” Dean snarled, and then he jammed the shank straight into Lucifer Pellegrino’s heart. Sam saw red as Lucifer’s blood spilled out all over Dean’s hands and wrists, dripping onto the ground.  The earth stood still as Dean was suddenly tackled by two guards, who pinned him to the ground as they wrestled the crude bloody weapon out of his hands. One of the guards brought out a pair of handcuffs and closed them around Dean’s wrist. Blood still covered the older Winchester’s hands and Sam was briefly reminded about the old days.

The courtyard was silent. All eyes followed Dean as he was roughly dragged away. Lucifer’s final command had been heard by all and they waited, eyes wide, to see if Dean would become the next Head of the Italian Mafia. Lucifer and Alastair’s bodies were taken away quickly and Gabriel was rushed to the ER, clinging on to life. Sam and Crowley were left standing in shock while Azazel, War and Pestilence stood staring stupidly as the corpses of their leaders were taken away.

“This has gone too far Moose,” Crowley sighed.

\-------

Dean walked into Castiel’s office, his posture confident, a smirk plastered over his handsome face. Castiel frowned as his attention was drawn to the freckles that dusted over Dean’s cheeks and nose. His favorite song played softly from the old record player that sat behind his desk, and he grimaced when he realized that unfortunately, the song was entirely inappropriate for the situation at hand, but he hoped Dean wouldn’t notice. Dean cocked his head to the side and listened to the airy song as the words danced out of the speakers; his smirk grew wider and his bright green eyes seemed to glow with an unsettling amount of sheer smugness.

_Take my hand,_   
_Take my whole life too,_   
_For I can’t help,_   
_Falling in love with you._   
_Like a river flows,_   
_Surely to the sea,_   
_Darling so it goes,_   
_Some things are meant to be._

“Elvis huh,” Dean said, plopping down in the chair in front of Castiel’s desk. “I can dig Elvis.”

“I really don’t care what you can ‘dig’, Dean. What I do care about however is what happened between you, Alastair Heyerdahl and Lucifer Pellegrino."

“Those sons of bitches had it coming. Lucifer stabbed Gabriel and drove my brother into insanity and Alastair was a massive fucking douche!”

“YOU KILLED THEM WINCHESTER!”

“I’ve killed a lot of people Novak,” Dean said, rolling his eyes and propping his feet on the warden’s desk. Castiel huffed and promptly knocked them off, earning another eye roll from the prisoner.

“You don’t think I know that already? I’ve read your file. I know all about your murders, both the ones that were proven to be you and the ones suspected. I don’t care that you killed people in the past Dean, I have my share of blood on my hands. The point is that you killed two prisoners, while still in jail!”

“And everyone can thank me later. They were part of the Italian Mafia. You think my murders were bad? You should have heard the fuck-time stories Alastair told me. He and Lucifer have killed, and have had killed, enough people to fill a nation! Compared to them, I’ve just been killing snails in the backyard.”

“Is that truly how you regard Human life Dean?” Castiel asked aghast. Dean chuckled and stood up slowly. He circled around the desk to leer over the warden.

“Only the lives of those who aren’t truly human. See Cas, most people in this world, are insects, pests. I take care of the liars, the cheaters, the corrupt. Sure my methods are a bit inhumane, but the people in question are inhumane. They don’t deserve to die quickly. So I torture them nice and slow, until they are begging me for death,” he leaned in closer, his lips inches away from Castiel’s. “Begging me for release,” he whispered, swiping the tip of this tongue across his lips hungrily.

Castiel pushed Dean away and shook his head. Dean growled in annoyance, but was pleased to find that hidden behind a layer of distain, arousal seeped through the warden’s bright blue eyes. Dean leaned forward again and froze when he heard the Taser being turned on.

“Winchester, you shall be escorted to isolation and you will remain there until I figure out what to do about this situation.”

“I need to speak to Sammy first.”

“No. You are no longer allowed to have contact with any of the other prisoners. If you need to get a message to your brother, you can ask me or one of the guards to deliver it.”

“Dammit Cas, just let me talk to Sammy for a minute.” Dean huffed, stomping to the other side of the desk and slumping in his seat, casting a heated glare at Castiel before dropping his eyes to the ground and muttering, “I just need to make sure that he’s okay.”

Castiel stared at the prisoner for a minute, trying to make sense of the sudden attitude change. In the course of one sentence Dean had gone from haughty and demanding to shy and insecure. It made Cas wonder if Dean was really who he was known as, or if there was a softer side hidden beneath all the bloodshed and hatred.   

“I’m sorry Dean, my word is final,” Cas said, folding his hands on his desk and looking Dean in the eye. “If I break the rules for one prisoner, then I would have to break the rules for every prisoner. And I’m not a rule breaker.”

Dean glared at him then let out a growl that had Castiel subconsciously reaching for his Taser. “Listen here you self-righteous prick,” Dean snarled, “You have no fucking idea what Sam and I have gone through, if I were to even indulge in telling you a fourth of our story, you would be running like your life depended on it; and if we weren’t in here, it probably would. So how about instead of pretending like you’re better than me, you grow a pair and step out from behind that desk.”

Castiel’s eyes narrowed and he tilted his head slightly, “I’m self-righteous? You do realize that the whole speech you just gave me was a speech about how I should be afraid of you. I have rules to obey so that this jail runs smoothly- obviously I’ve been way too soft on you already.” Castiel got up from his chair and crossed over so that he was face to face with Dean, his hands pinning the prisoners wrists to the chair, his voice dropping dangerously low. “Listen to me, Dean Winchester,” he growled, blue eyes sharp, piercing, calculating, “I may not know much about your life story, but I do know more about your story than you know about mine. Your mother was the loving one, always there, always caring. Your father on the other hand was an abusive drunk, cold, distant, never seemed to care about you. You had to raise your brother, which is why you have such an unhealthy need to parent him-and don’t tell me that’s not true because you just killed two men in an attempt to do just that. Now, I suggest you go quietly to isolation. Otherwise I would be more than happy to taze you, or have you put in a straitjacket.” At some point during his speech, Castiel had moved his face over so that his lips almost touched Dean’s ear with every word. He was surprised to find that Dean’s forehead was resting on his shoulder and his breath was ragged. Castiel allowed them to stay like that for a moment before coldly shoving the prisoner away and sending his best glare in Dean’s direction as he called for the guards to escort him to isolation.

\-------

Dean was still grappling for control of his body as he let himself be led quietly down the halls to isolation. The warden had been scarily right about everything and something about the way he stood so close and had just let Dean rest on his shoulder had awoken a need that Dean wasn’t even aware he had. He wanted to run back to the warden and feel his hot breath against his ear again. He wanted to bury his face in those firm shoulders. He wanted contact, but not with sex as the end goal. Then he remembered what Lucifer had said.

_My final rule is this; you have twenty-four hours after killing me to make the Warden your little bitch. Fail, and both you and your brother will be killed, succeed and take my place as Leader of the Italian Mafia._

Dean caught a glimpse of one of the guards' watch as the door to his new cell was unlocked and he was thrown inside. Six hours had already passed since the incident. He crossed the cold cell and sat cross-legged on his cot, wracking his brain for a plan.

**Notes for the Chapter:**

> So there you have it. Gabriel, Lucifer and Alastair are all dead. Dead has to make Castiel his bitch otherwise he and Sammy are dead too. Yes, all the characters that I just killed are dead dead. No they will not be returning. There will however be two new someones who come in very soon and I'm sure that you will absolutely hate them.
> 
> If you have any questions or want little updates follow me on Instagram @iamsmauglocked
> 
> Idk if anyone has fanart but if you do feel free to send it in to miss.tck@gmail.com


	10. Chapter 10

**Notes for the Chapter:**

> So sorry this took so long (again) 
> 
> Also, a huge thank you to my wonderful BETA, Meg, you are truly amazing and I am so happy to be working with you! <3

Dean grabbed Castiel’s uniform and shoved him face first against the cell wall.

“Every damn day you tell me what to do,” he snarled against the back of Castiel’s neck, “and every damn day I have to listen. But it’s night time now Cas, Lucifer and Alastair are gone, and you’ve woken the demon.” At this Dean started grinding hard into Cas’ ass. He purred at the low whimper that escaped from Castiel’s mortified lips and, still pinning the warden to the wall with his body, he slid one hand into Castiel’s hair and the other one to his crotch. “Let’s see how tough you really are, angel boy.” He sneered as he pulled back hard on Castiel’s hair and grabbed the warden forcefully through his uniform, his hips grinding even harder into the man’s rear. Castiel tried to push away but Dean wasn’t going to have any of that, not tonight. If this guy wanted to play hard to get, he could do that after this was over, but tonight Castiel was his prisoner. Not the other way around. And with the way Castiel had been ordering him around, well, that was as good as if he’d bent down to pick up the bar soap.

Castiel was stuck, pinned to the cold brick wall of his own jail by easily one of the most dangerous prisoners in the building. _Why did you have to come by yourself? He just killed his cell mate and the head of the Italian Mafia you dumb fuck!_ a small voice in the back of his head scolded. The thought was quickly replaced by fear and a hint of something else… wait, was that pleasure? Oh hell no! No way could he be getting even the slightest bit of pleasure out of this. Dean Winchester was about to rape him and here he was, a part of him enjoying it?!? No, not him, not ever. “Winchester, back away now,” he growled, surprised at the power in his voice, grateful that his steely resolve had not crumbled past the point of no return.

“Make me,” the prisoner smirked, nipping at the warden’s ear, slowly licking down his neck. Dean latched his lips to Castiel’s neck and proceeded to suck a long line of hickeys for everyone to see, claiming the warden as his property. He ground into the backside of his captive even harder and started to grope him in time with each of his thrusts. He pulled on Castiel’s hair as he nipped at the soft flesh at the base of his jaw. The warden hissed and tried once more to get away. “Silly warden. Don’t you know that this is the reason I got locked up in the first place? Sure they only caught me for the harm done to that slut Meg, but there were others, so many others. Male, female, it doesn’t really matter to me. As long as it’s some place to shove my dick, I’m happy.” He could feel Castiel stiffen beneath him and he let out a dark chuckle and removed his hand from Castiel’s hair, placing it instead over his stomach, pulling up the front of his shirt slightly. “You thought that just because we’ve been playing nice you were safe didn’t you? Well, that is generally how I play. See they leave all the good stuff out of the reports. Sam would play the douchebag, the needy grabby irritating horny jerk who was just a little too pushy and way to desperate, then I would swoop in and lure them into a false sense of security, safety if you will. People are all the same, show them a contrast and they immediately jump for the nicer one. They don’t bother to look behind the sheep’s clothing to see the wolf. The real question here is, are you going to make me happy Cas? Or are you going to try and deny me?”

Just then, Castiel reared his head back and it made contact with Dean’s face. There was a sharp crack as Dean’s nose broke, he swore and backed off immediately, cursing in pain. Castiel whirled around to see the prisoner holding his nose gingerly, caught in the crossroads of wanting to pinch it to stop the bleeding and being in too much pain to even touch it. His emerald green eyes screamed murder and Castiel wasted no time in pulling the Taser from his pocket and firing it at Dean, then he ran out of the cell and locked it up quickly, not looking back at the convulsing prisoner. He rushed down the hallway to the infirmary to let Dr. Balthazar know that prisoner W1121983 had been tased and probably had a broken nose and would more than likely need to be fully put under before being brought into the infirmary, before he continued hurriedly back to his office. Once over the threshold, he slammed his door and sank to the floor, shaking and silently sobbing. Prisoners had tried to have their way with him before, that wasn’t new, what was new was that out of all of them, Dean Winchester had controlled him the longest. If he hadn’t been able to break his nose, he would probably be being fucked six ways to Tuesday right now against that cold, harsh brick wall. Worst of all, he knew that a small part of him would have enjoyed being controlled like that. Castiel barely made it to the trash can before he started throwing up all the food that had been tossing uncomfortably in his stomach since the moment Dean had pinned him down. After a few final dry heaves, he sat back up and walked over to his personal bathroom. He splashed some icy water onto his face, then grabbed his spare toothbrush and squirted some toothpaste on it, vigorously scrubbing his teeth while he recounted the events leading up to being pinned down, humped, and groped by Dean Winchester.

 

\---

 

“Prisoner W1121983 has asked to speak with you sir,” Anna Milton stated, her strong quiet voice drawing Castiel’s attention away from the prison report he was currently working on.

“Thank you Ms. Milton. I will make sure to speak to him when I get the chance. Did he say what he wishes to speak to me about?”

“No sir, just that he wishes to speak to you in private,” Anna replied, tucking a strand of red hair behind her ear.

“Alright,” Castiel sighed, meeting the gaze of his deputy. “I’ll speak to him before I leave. Is there anything else?”

“Yes sir, now that Prisoner P56660503 is dead it seems Prisoner W1121983 has taken his place. Also, Prisoner W02012006 has requested a permanent transfer to share a cell with Prisoner S02150519, should he survive.”

“Prisoner P56660503, which must be Lucifer Pellegrino correct? W02012006 is Samuel Winchester? Remind me who Prisoner S02150519 is.”

“Gabriel Speight sir, he’s the con-artist who Lucifer stabbed,” she said walking forward and placing five large files onto Castiel’s desk.

Castiel sighed and ran his fingers through his messy dark hair. “Thank you Anna. If that’s all you may go home early. Tell Michael and the children I say hello.”

“Thank you sir. See you tomorrow.” Anna smiled, pausing once she reached the door. “Oh I almost forgot, Officer Harvelle called earlier wanting to talk with you. She asked me to tell you to call her back when you got the chance.”

Castiel smiled and nodded at Anna, bidding her a good night as he picked up his phone and dialed Jo’s number.

“Officer Harvelle speaking, is this an emergency?”

“Nope, it’s just your favorite Warden giving you a call back.” Castiel chuckled, leaning back in his chair and flipping absentmindedly through Dean Winchester’s file.

“CASSIE! Long time no chat!” Jo grinned through the phone, Castiel heard another female voice in the background saying something and then Jo responding with, “I know right, look who finally decided to call me back! So assbutt, Charlie and I are both curious how come it took you so long to return my call? Prisoners causing a ruckus?”

Castiel laughed, “That’s an understatement. I feel like I’ve been pinned to the ceiling and forced to watch this whole place go up in flames. Today a Mafia boss killed a con-artist, and then one of the prisoners killed the Mafia Boss and his second in command because they were driving his younger and also murderous brother, whom said con artist had the hots for, crazy, and apparently they were also sexually harassing both brothers.” He grimaced at a photo of a young woman sprawled out naked on a blood soaked bed, throat slit, skirt hiked up, underwear at her ankles. Bella Talbot _. Suspected victim of Dean Winchester. Not enough proof to condemn._

“Wow, Charlie and I may just have to take a day off work and bring some popcorn. Nothing like an inmate murder to keep the flames of my passion for the justice system burning.”

Castiel rolled his eyes, “You better not let your mother hear you say that, I’m pretty sure Chief Harvelle doesn’t want her only daughter encouraging dangerous prisoners to murder each other. HR is going to have my ass because of this. They might even send in Dick Roman.”

“Shit.”

“Yeah, he’s such a… well he’s a dick.”

Jo laughed and Castiel felt the corners of his lips twitch up. “So enough about my issues, why did you call me?” he asked, putting down the elder Winchester’s file and picking up the younger’s.

“Oh, right! Charlie and I are having a Star Wars marathon tomorrow and we wanted to know if you’d like to join? It’s a Friday and I know for a fact that you have Saturdays off so I’m not going to take no for an answer.”

“We’ll see, I’m going to have to log a few extra hours tomorrow because of what happened today, but I’ll do my best,” he replied, turning the pages in Sam Winchester’s file from one suspected gruesome murder to another. Sam’s file held more credit card frauds as well as the illegal purchasing and selling of weapons then it did murders and Castiel figured that the younger brother was probably the brains behind the crimes.

“He said ‘we’ll see’.” He heard Jo say to the other female voice, “Hey Cassie, Charlie wants to- hey!”

“Castiel Novak, if you don’t get your ass over here tomorrow with a six pack of beer and a bottle of whiskey, I will personally hack into your prison database and label every file ‘assbutt’.” Charlie’s voice was playful, but Castiel didn’t doubt that she would do just that, maybe not every file, but she would find a few of the less important ones and mix them in with the high priority ones, causing hours of extra work for Castiel.

“Fine, you win,” he sighed dramatically, closing Sam Winchester’s file and setting it atop his brother's. “What time should I be there?”

“YAY!” Charlie squealed, “I’d say as early as you can, we’ll wait for you until 7:30, but any later than that and you’ll just have to deal with wherever we’re at.”

“Deal,” he said, standing up and stretching, “Hey Charlie, I have to go talk to one of the prisoners now, but I’ll see you and Jo tomorrow. I should be able to be there around 5 or 6ish depending on how the prisoners behave.”

“Sounds like a plan. We’ll see you then!” Charlie said and he could hear her smiling.

“Don’t forget the booze!” Jo chimed in the background.

“When have I ever forgotten the booze?” he grumbled jokingly and grinned when he heard Charlie started laughing followed up by Jo asking “What? What did he say?”

“Bye Cassie! See you tomorrow!” *click*

Smiling, Castiel grabbed a piece of paper and a pen and wrote himself a reminder about the movie marathon, and then he packed away the files into his briefcase and set it on his desk. Time to go see what Mr. Winchester wants, he sighed. Making his way down the cold halls to the cell of Prisoner W1121983, he wondered if he should have brought back up, his mind recalling the pictures of Dean Winchester’s supposed victims and the murder that happened the day before. No, why would I bring back up this time? I dealt with Mr. Winchester yesterday and we seem to have an agreement. He knows who’s in charge of this place. To bring back up now would only show weakness. I have a reputation to keep.

 

\---

 

That’s how he ended up shaking at his desk, head in his hands, silent sobs wracking his entire body, tears streaming down his face, the stench of vomit filling up his office. He sat like that for the better part of an hour, trying hard to regain enough of his composure to make it out of the prison without letting it slip that he was terrified of what Dean Winchester had been about to do to him. If Dean, or any of the other prisoners knew for just one second how close Dean had been to completely overpowering the warden, Castiel would be finished. He took several deep cleansing breaths and made his way back to the bathroom to splash more water onto his face. He took his time drying off, studying his face in the mirror. He looked tired, his scruff was a little bit too long, his eyes were red and his eyelids were puffy. His nose was still a little runny and he grabbed a tissue, held it to his nose and blew. He was still shaking, but as long as he didn’t bump into any of the prisoners and as long as he kept his posture straight and walked out of the prison looking confident, none of them would be the wiser. He went back into his office, gathered up his belongings and strode out locking the door behind him, moving quickly through the halls, out the front door; he successfully made it into his car before the tears started flowing again.

**Notes for the Chapter:**

> I don't know if you caught it or not, but the prison numbers mean different things! Here is what each prison number means:
> 
> Dean Winchester’s prison number (W11211983) Is Mary’s death date in the TV series. 
> 
> Sam Winchester’s prison number (W02012006) is the season, episode and year of John’s death date in the TV series. 
> 
> Lucifer Pellegrino’s prison number (P56660503) is the number of actors who portrayed Lucifer, followed by the devils number along with the season and episode that Lucifer was first portrayed by Mark Pellegrino, also Lucifer’s last name is Pellegrino because of the actor. 
> 
> Fergus Crowley’s first name is Fergus because his human name in the series was Fergus Rodric MacLeod, his prison number (C51016613) is the season and episode which he first appeared as well as his birth year, the 3 at the end is how many inches of willy he sold his soul for. 
> 
> Gabriel Speight’s last name is because of the actor, his prison number (S02150519) is the season and episode he was first introduced, followed by the season and episode he was killed. The letters in front of the prison numbers are the first letters of their last names. 
> 
> Note: This isn’t at all the way prison numbers are usually (aka, in real life), but I wanted their prison numbers to be little eggs that if people picked up on it would be cool. I enjoy small detail like that. Of course, none of these dates/numbers really mean anything in this AU to the characters, they are just numbers that they’ve been assigned.


	11. Chapter 11

**Summary for the Chapter:**

> In which Sam remembers, Cain saw, Azazel is a giant bag of dicks, Balthazar is worried and so is Dean, and Castiel is more then just not okay.

**Notes for the Chapter:**

> I'm so sorry this took so long to post. I made this deal with myself that I wouldn't ever post a chapter until I sent the next one in to my BETA to be edited and between being sick, writer's block, exhaustion and just plain old procrastination, Chapter 12 took forever for me to write (and it's not even that long of a chapter.) Anyways, I hope you like this one.

The next morning found Folsom Prison in a hazy trickle. The inmates were unusually quiet and it seemed as if the whole building was holding its breath. Sam Winchester sat on his bunk, only leaving to grab food during mealtimes. He didn’t talk to anyone and no one came to visit. A few of the prisoners would walk past his cell and Cain had moved from the courtyard to inside, Sam suspected that it was so that someone could always have eyes on him. He sat there thinking, remembering, praying that it hadn’t really happened. Gabriel was dead, Lucifer was dead, Dean was gone and there was a very good possibility that both of them would be dead by tonight. No way would Dean ever go through with raping Castiel; he was too fond of the blue-eyed warden to ever do that.

Sam closed his eyes and buried his face in his hands and let out a silent sob, everything had gone so wrong. When he was younger, he wanted to go to Law School and become a Lawyer, to work in Washington and to help people. Now, here he was, sitting in a jail cell, mourning the fact that his Mafia Boss lover was dead and reminiscing over the death of the con-artist he had accidentally fallen in love with. He would never be able to see either of them again, he would never again feel Lucifer’s gentle touch as they fell asleep wrapped around each other. He would never know what it was like to kiss Gabriel and hold him close, keeping the trickster out of trouble for at least a little while. All he was left with were memories.

Memories of the time he first met Gabriel, the flirting in the courtyard, spending all day just talking to each other and becoming friends. Memories of when they had teamed up to play tricks on Crowley, simply to get a reaction. Memories of having a real friend for the first time in his life, a friend who didn’t run away when he heard the whole story, a friend who had given him a hug and said, “It’s okay Sammy, just because you’ve done some bad things does not make you a bad person. You are one of the best people I know.” Memories of Gabriel’s laughter filling the air, and his smile infecting everyone who saw it, of how he would rub the back of his neck when he was flustered and shoot suggestive winks at Sam during random parts of a conversation. Memories of the golden haired man who had loved him unconditionally, no matter how many times he showed up late to breakfast because he and Lucifer had engaged in some morning activities.

He remembered when Lucifer had first kissed him, sitting on the floor while the Mafia boss straddled him and explored his mouth, licking every corner and claiming it as his own as they rubbed hotly against each other. He remembered the first time they had sex, slow and loving and still a little bit rough, exactly what Sam had needed. He remembered teasing Garth while Lucifer was getting ready for bed and then wrapping his limbs around his cellmate, feeling his lips curve up into a smile against Sam’s neck as they held each other close. He remembered the first time Lucifer got rough, slamming into him barely prepped, pulling the dirtiest moans from Sam’s throat, both of them yelling and groaning so loud, neither could speak the next day and Sam could hardly walk. He remembered the nights where they would just lay in the bed, huddled up close, planting light kisses and falling asleep to the sound of each other’s heartbeats.

He remembered when Lucifer had told him to stay away from Gabriel, the day when everything had started to go south. The day when he realized that it was all too good to be true. His eyes had been opened to what his brother had been going through and it made him sick to think that while he was basking in the affection he was receiving, his older brother, his only family, was being raped and tortured right under his nose. He learned that Lucifer had been a part of it a few times, and that there were several occasions when the Mafia boss had pinned Dean against a wall and jerked him off through his jumpsuit. Sam had returned to the cell that night unable to look at his cellmate; the next morning was the first time Lucifer had raped him. After that day, he did anything the Mafia boss told him to do. He avoided Gabriel and Crowley, leaving them without so much as a goodbye, let alone an explanation.

Now Gabriel was dead, he would never know that Sam hadn’t wanted to stop talking to him. He would never know that Sam had fallen so madly in love with him it was hard to think straight every time he looked him in the eye. Gabriel would never know that he was the most important person in Sam’s life and that if he had the chance; Sam would have repeated every mistake just so that he could eventually meet Gabriel in Folsom Prison. Lucifer was dead too, leaving his impossible final command along with new scars and new baggage that Sam would carry for the rest of his life.

\---

Five cells down, Pestilence and War joined Azazel and Cain to discuss the events of the day before.

“Dean completed his task,” Cain began after the other three men had settled down. “The Warden has called in ‘sick’ and they are sending a replacement soon. Rumor has it that a man by the name Dick Roman will be taking over.”

“Just because Cassie called in sick, doesn’t mean that Winchester completed his task. How are you so sure?” Azazel asked, squinting at Cain who glared back before rolling his eyes and drawing out his phone. He clicked a few buttons then showed them the screen.

_“Let’s see how tough you really are Angel boy,”_ Dean sneered through the screen. They watched as Dean ground his hips into Castiel’s rear and groped the wardens testicles.

The video cut out after a minute and Cain showed them the next video. This one showed Castiel, ghostly pale, tears streaming down his face, running out of the jail. His clothes were rumpled and his shirt was half way unbuttoned and untucked, dark hickeys covered his neck and his hair was tousled in a way that screamed sex. He was unaware of the man in the shadows, recording him as he got into his car. Then, he was sitting in his car, sobbing.

The video stopped and Cain looked smugly at the men standing in silence. “As I said,” he grinned, “Dean Winchester has completed his task.”

Azazel looked once more at the screen of the phone which was now frozen on Castiel’s sobbing figure, then he nodded and smirked.

“Seems he had it in him after all,” Pestilence chuckled, “What does this mean that we do? He is still in isolation so there is no way we can talk to him.”

Cain shot Pestilence a bored look and then gestured pointedly at his uniform. Pestilence muttered a small “oh, right” and then fell quiet.

“I say someone should inform Sam,” War said, lazily picking at his fingernails and then looking up when no one said anything. “If Dean is now our fearless leader I’m sure his baby brother will want to know. Also, if we’re the ones who tell him then we’re the ones who get to see the look on his face when he hears that his big brother raped the warden,” War laughed grimly, a light gleaming in his eyes.

Azazel and Pestilence shot each other grins and Cain looked unimpressed by War’s reasoning but nodded in agreement all the same. They sat in the cell for another hour discussing the events of the days previous before Cain announced that he had to get ready for his shift and left without another word. War and Pestilence left shortly after in favor of getting some food and after they left, Azazel decided it was time to pay a visit to baby Winchester.

\---

Sam was curled into a ball on his bed when he heard a pointed cough from the doorway of his cell. He grimaced and slowly turned to face his visitor. Azazel was leaning against the door frame and he grinned when their eyes met. He reminded Sam of a snake who had just caught sight of a wounded field mouse.

“What do you want,” Sam asked, his voice had an unusual raspy quality from screaming yesterday and his throat hurt.

Azazel’s grin turned to a frown and he walked across the cell and sat on the edge of Sam’s bed. Sam sat up and glared at him, scooting to the other end of the bed, eyes carefully trained on the unwanted guest.

“I’m just here to tell you congratulations,” Azazel said, his smile returning when a look of confusion passed over Sam’s face, “Your brother made the warden his bitch last night which means that he is officially the head of the Italian Mafia. Of course because you’re his baby brother, you’re on the no kill list.” Sam’s face was now a look of pure horror as the new information settled. Azazel stood up and patted him on the shoulder. “Looks like that slut Gabriel didn’t die for nothing, huh? Although, he really should have stayed away from the boss’s property, just because they’re cousins doesn’t give him the right to share.” Azazel laughed darkly at Sam whose eyes were wide.

“C-cousins?”

“Oh, you mean you didn’t know?” Azazel smirked, “Gabriel and Lucifer used to be quite close, before Lucifer and Michael stopped seeing eye to eye and started seeing blade to blade. That’s when Gabriel jumped ship and took his little sister far away. I guess you can’t deny what’s in your blood though, cause he still became a criminal. Sure he was fucking useless and quite frankly, a disgrace to the family line-”

Sam’s fist hurtled through the air and hit Azazel square in the nose, there was a sound crack and then Azazel felt blood gushing down his face. He swore violently and lunged at Sam, landing a few decent punches before Sam had him pinned to the floor. Azazel twisted violently under Sam, but to no avail.

“Don’t you ever say anything bad about Gabriel ever again,” Sam growled low in his ear, “In fact, I don’t ever want to hear you saying his name. You are a fucking worthless piece of shit and you are not worthy enough to speak of him. Got it?”

Azazel grinned and felt blood trickled into his mouth, “Gabriel was a fucking freak, he deserved to die.”

The last thing Azazel saw was Sam’s fist speeding downwards towards his face, and then everything was black.

\---

“Here’s another one for you Balthazar,” Garth said as he hauled Azazel into the infirmary. Balthazar heaved a sigh and helped Garth lay Azazel down in one of the beds.

“I’m going to need a statement from you regarding the attack,” Balthazar told Garth, walking over to retrieve a statement sheet and a pen, which he handed to the guard who nodded that he understood.

Balthazar did the routine check and found that Azazel had a mild concussion and a broken nose, nothing too serious. He thanked Garth after receiving the statement and placed it carefully in Azazel’s file.

“So, are you going to tell me who did this?” he asked, looking curiously at his newest patient.

“No, that would be a waste of both our time,” Azazel retorted, looking bored and obviously trying to hide that he was in pain.

“Very well dear, if you change your mind I will be in the other room looking after my other patients.” With that, he walked out the room and walked to the room on the other side of the hall.

“Mr. Winchester, how are you feeling today, a little shocked perhaps?” Balthazar smirked as Dean rolled his eyes.

“I’m fine, my head still hurts but I’m fine,” Dean grinned, touching his nose gently. Then he became very serious, “how’s Cas?”

Balthazar grimaced, “Cassie left in a hurry after last night’s events, and he called in sick today. They are sending someone to take over while he takes some time off.”

Dean looked down at his hands which were now folded in his lap. “But how is he?”

Balthazar studied the prisoner for a moment before walking across the room and sitting in the chair beside Dean’s bed. “Honestly, I would be very surprised if he’s doing okay. What you did last night… what you tried to do last night. What were you thinking? Castiel has never been anything but nice to you, in fact if you were to ask me I’d say that he had it soft for you. I’ve never seen him sidestep so many rules for anyone before. You do know that with all the trouble you’ve caused since you arrived, not including the fact that you murdered two of your inmates, he should have had your ass sent to one of the federal prisons in DC a long time ago.”

Balthazar was startled when he saw a tear slide down Dean’s face and he looked hard the Winchester. For the first time he noticed how tired Dean looked, how young and how troubled he was. This man had been through more than any man his age should ever have to endure, and he carried it all on his shoulders. Balthazar looked away and then stood up. “I’m going to give Cassie a call and see how he’s doing. I’ll let you know as soon as I know,” he said, the corners of his mouth twitching up when Dean’s face lit up with hope.

Balthazar walked out of the room and went over to his office. He sat at his desk and picked up the phone, dialing Castiel’s cell. It rang a few times before someone picked up.

“H-Hello,” a female voice said through the speaker.

“Hello dear, this is Balthazar; I’m a friend of Cassie’s. Who is this?”

“Name’s Charlie, Cas- Cas can’t talk right now.”

Something in the way she had said that made Balthazar suddenly very worried. His stomach dropped and his mouth went dry.

“What do you mean he can’t talk right now? Is he okay?”

He heard Charlie sniffling through the other end of the phone and then she was crying. “He- he was in a-an accident last night,” she whispered, “I don’t know exactly what happened but-but… well he’s in the hospital right now and the doctors are saying that it doesn’t look good. And his car- oh god his car- it’s a total wreck! He drove straight off the road into an abandoned farmhouse and the whole thing just collapsed. T-the people living across the street, they heard the crash and called 911 immediately b-but the doctors are saying that he may have fractured his collarbone and there might be damage to his spine. His arm is definitely broken and so are some of his ribs but they can’t be sure about anything else until he wakes up – if he wakes up.” Then she was crying again and Balthazar couldn’t do anything but listen.

“Charlie,” he said after she had calmed down, “what hospital is he at?”

“Serenity Valley, it’s just off the-”

“I know where it is, I’ll be there as soon as I can.”

**Notes for the Chapter:**

> First Gabe, then Luci and Azazel and now Cas' life is on the line. Oops.


	12. Chapter 12

**Summary for the Chapter:**

> In which Castiel is at the Hospital.

**Notes for the Chapter:**

> You are going to want to read the End Notes.
> 
> Also, don't skip what's in italics. Trust me. It's important. Every detail is.

_Castiel was running. He didn’t know where he was going to end up; only that he had to escape. Black figures ran after him, leaving trails of black goo in their wake and hissing promises of death. He made it to the end of the street before the lights went out and suddenly he was falling, he looked up and saw the figures looking down at him, watching him descend into the void. Then he was in a white room, the contrast was blinding and it took a moment for him to adjust. There was a woman sitting at a white desk. Her red-brown hair was pulled back into a low bun, her bangs swept neatly to the side. She paid no attention to Castiel and just sat there, her blue eyes staring blankly at the wall opposite her. He watched as a short man with curly brown hair snuck up behind her, Castiel screamed a warning that fell on deaf ears and he watched helplessly as the man drove a metal instrument deep in the back of the woman’s head. She fell face forward onto the desk and a steady stream of red seeped from her skull and onto the pristine furniture. The man smiled down at her corpse and rand his finger through her blood, before he turned around and started writing on the walls with it. He drew some sort of symbol and then turned to stare directly at Castiel. The man shot Castiel a truly evil smile before slamming his palm on the symbol which erupted in a blinding white light._

Castiel blinked a few times and moved his head slightly. Everything hurt, his head was trying to crack itself in half and his limbs seemed to have weights tying them down. He let out a small moan that scratched his dry throat and made him cough. Within an instant he saw a flaming red blur standing over him.

“Cassie?” Charlie’s voice called out from somewhere far away. He blinked a few more times and slowly her worried face came into focus. She looked terrible, her red hair was pulled back into a messy ponytail with a few stray hairs hanging loose around her face, and there were dark circles under her bloodshot eyes.

“Charlie… are-are you okay?” Cas asked, looking worriedly at her. She laughed and cupped his face, touching their foreheads together.

“I’m fine Cassie, just fine. You however, the doctors didn’t think you were going to make it through,” she whispered, pulling away and running her fingers through Castiel’s tangled hair.

“What happened?”

“I was going to ask you the same thing,” she sighed, “all anyone knows is that according to Balthazar you tased some prisoner, then an hour or so later a man living in the farmhouse twenty minutes from the prison said that he woke up to the sound of metal against something and that there was a man unconscious in a car wreck across the street.”

“They had to use the Jaws of Life to get you out…” said a small voice from the other side of the room. Castiel looked over and saw Jo rising out of the chair she had probably been sleeping on and stretching before she crossed over to the bed. “When they did get you out, well they told us that if you survived it would be a miracle.”

“I knew you were going to make it,” Charlie said, a smile pulling at her lips, “how could God ever let this little angel die before he even gets laid?”

Castiel rolled his eyes and Jo let out a bemused laugh followed by a light punch to Charlie’s shoulder which gained an “ow!” from the redhead.

“So what happened Cassie?” Jo asked, looking back at Castiel. “When we spoke on the phone you sounded fine, I mean you mentioned that there had been an incident-”

“Yeah, what was it, like three murders?” Charlie interrupted.

“It was nothing,” Castiel lied, looking away from his friends, “I probably just fell asleep at the wheel.”

“Bullshit,” Charlie said, gently grabbing his chin and forcing him to look her in the eyes. “Castiel Novak, you listen to me, I have been sitting here for four days while you were in a coma, with no guarantee that you were going to come back. Jo and I cancelled the Star Wars marathon! So I am going to get the truth because there is no way that Castiel Novak fell asleep at the wheel. Especially not after having to taser a prisoner, we all know why you have that taser in the first place so out with it.”

Castiel glared at her and then sighed, “Fine, help me sit up.”

Jo and Charlie helped him maneuver his way into a comfortable sitting position, which proved to be difficult seeing as how his left wrist was broken and so were several of his ribs. He noticed that both Charlie and Jo were in their pajamas and Charlie’s overnight bag was sitting against the wall next to the chair Jo had slept on. A nurse walked in while Charlie and Jo were dragging chairs over to his bedside and they all had to wait while the nurse checked Castiel to make sure he was okay. She looked very familiar and Castiel had the vague feeling that he had seen her somewhere before. He studied her while she asked him various questions.

“Who is that?” Castiel asked Jo while the nurse talked to Charlie.

“That’s Naomi Speight, she’s your nurse,” Jo whispered back, watching as Naomi and Charlie spoke, “I don’t like her very much…”

“Why not?”

“It’s hard to explain,” Jo sighed, looking back at Castiel, “there’s just something off about her. I don’t know it’s probably nothing.”

Castiel shot Jo a worried look and then turned his attention back to the nurse. It wasn’t until later that night, after he had told Jo and Charlie about what happened with Dean, and after he insisted that they go home and sleep in their own beds that he realized why Naomi looked so familiar. She was the woman in the white room in his dream that the man with the curly hair had killed. He shivered in his bed and curled up into a ball under his blankets. He fell asleep thinking about a convict with bright green eyes and dirty blonde hair.

The next morning he awoke with a start, Naomi was fiddling around with his IV.

“I’m just changing out your pain killer,” she explained, smiling sweetly.

“Okay,” Castiel nodded, staring at her quizzically, “Jo said that your last name is Speight…”

“Jo is correct,” Naomi responded, writing something down on her clipboard and then sitting down in the chair next to Castiel’s bed. “Is something wrong?”

“Do you have any relation to Gabriel Speight?”

Naomi nodded sadly, “yes, Gabriel was my brother. I read in your file that you are the warden at the jail he was sentenced to.”

“Folsom Prison, yes,” Castiel said. “I’m very sorry for your loss. He was one of the good ones, as far as prisoners go. He didn’t deserve what happened.”

“I don’t blame you Castiel. I do blame Lucifer though. Did you know that we’re cousins? I just don’t understand how you could kill someone, especially if they are family.” Naomi sighed and Castiel could see the sorrow and confusion in her eyes.

“If it makes you feel any better,” he said, “Gabriel died trying to save someone he cared a lot about.”

“I know, Sam Winchester right? He’s mentioned him a few times when I came to visit. Is Sam okay?” She asked, looking genuinely concerned.

“As far as I know yes,” Castiel replied, “Dean, Sam’s older brother, killed both Lucifer and Azazel after Lucifer killed Gabriel.”

Naomi gasped and then nodded and asked “Do you know what Dean’s mission is?”

Castiel tilted his head, “What do you mean ‘mission’?”

“Well as I’m sure you know, Lucifer is… sorry, was, the head of the Italian Mafia. Gabriel said that Dean was being trained to take over the prison side of things once Lucifer and Azazel’s time was up. Knowing Lucifer, if he knew Dean was going to kill him, he’d probably threaten Dean with something. For example, ‘do this or else…’ He would have made it something very personal on both ends. Something that he knew Dean wouldn’t want to do, but something that would show that Dean is capable of taking over.”

Castiel’s eyes widened, “something like rape the warden?” he whispered.

Now Naomi studied him, “yes, I suppose that would definitely be a possibility. But Dean would have to make it very convincing. So convincing that even the victim would believe that he was a genuinely bad person.” Castiel felt Naomi’s eyes on him as he picked at his fingernails, processing the information.

 _Maybe Dean didn’t want to do what he did. Maybe his life depended on whether he succeeded or not. Maybe Sam’s life depended on it. But Naomi said that it would be something that he didn’t really want to do. What if this was all a misunderstanding. No. NO! He still tried to rape you! And if you hadn’t tased him, he would have succeeded._ Castiel sighed and rubbed his forehead. _This whole situation is so fucked up. Why did you have to fall for a prisoner Novak? How could you be so stupid! How could you let all this happen under your nose?_

“Castiel… Castiel? Hey, Castiel are you okay?” Naomi shook him and he was transported back to the real world.

“Y-yes, I’m sorry. I was just thinking over a few things,” he said, casting her a tired smile.

“Mr. Novak, is there anything you would like to tell me about the night of the crash? Something that perhaps you left out because you were too embarrassed?” She asked, her face was soft and gentle but her eyes were firm and serious, her pen was at the ready and she had already flipped the papers on the clipboard to the ‘notes’ section. Castiel looked at her for a minute and then shook his head.

“No,” he said, “I’m alright. However, if you could call Balthazar, the doctor at Folsom Prison, I would very much like to speak with him.”

Naomi looked at him for a moment before she nodded and stood up, “I will contact him and see if he is available for a visit,” she said, and then she was gone.

**Notes for the Chapter:**

> Warning about Chapter 13:
> 
> Hello everyone, so as all of you lovely readers are aware, I have not been shy with the matter of sex and mentioning rape. I am here now warning you that in chapter 13 there is a semi-detailed rape scene between two characters that you probably won't feel comfortable with at all. I didn't go into much detail because I honestly hated writing it but it was necessary for the continuation of this story. 
> 
> It is going to take a little while before I post Chapter 13 because of two reasons  
> 1) I still need to write Chapter 14  
> 2) Chapter 13 has not been edited yet
> 
> Another warning is that from here on out we are going to dive into a few different story lines. The fic so far has been mainly from Dean and Cas' POV but from now on we will have other Characters (ie. Balthazar, Crowley, Charlie etc.) "narrating" the chapters. Hopefully this will have the effect I want. Just realize that every chapter is very important to the story line, I strongly recommend NOT skipping chapters based on how interesting you find that characters story, otherwise you will be confused. Also, I know that I myself skip over the parts in italics a lot whilst reading other fics, DON'T. Even Castiel's dream in this chapter will prove to be important in a later one. Everything is written for a reason. Even this here End Note. 
> 
> Love to you all, thank you so much for sticking through this fic. I have no idea how much longer it is going to be but I will let you know once we are nearing the last few chapters. 
> 
> For fun times, follow me on Instagram @iamsmauglocked
> 
> Please give a big "Thank You" to my wonderful beta Meg, who puts so much effort in correcting my mistakes and offers up such amazing ideas for how to progress this fic. Without her, I can guarantee this fic would not be the same.


	13. Chapter 13

**Summary for the Chapter:**

> In which Dick Roman is a dick, Dean needs saved, and Balthazar realizes that Dean and Castiel care deeply for each other.
> 
> Also in which the author apologizes profusely and then runs and hides.

Dick Roman decided to take his sweet ass time showing up to take over Folsom Prison. That being so the Chief of Police, Ellen Harvelle, was asked to step in until he arrived. She was a middle aged woman who was rough around the edges but secretly very sweet and caring. Head Detective Jody Mills was assigned to assist Ellen in making sure everything was ready for Dick Roman’s arrival.

Jody had snuck Balthazar Dick Roman’s file after she heard how close he and Castiel were. Ellen had been upset when she found out, but calmed down after Balthazar promised that he hadn’t shared the information in the file with anyone else.

From what Balthazar gathered, Dick Roman was one of the top dogs in D.C.; on his first big assignment he had led a group of special ops, codename Leviathan, to take down the head of the Irish Mafia, Patrick Ozsan. Roman had captured and tortured Ozsan’s lover, Lia Hutton, in a successful attempt to draw the Mafia Boss out of hiding. When Ozsan showed up at the meeting place there were no negotiations, just five bullets which were shot into the heads of Mr. Ozsan, Ms. Hutton and the three men Mr. Ozsan had brought for protection.  The victory is what made Dick Roman big. He weaseled his way into creating his own task force which he named “The Leviathans” and under his leadership, they quickly rose to the top of the food chain.

When Dick Roman finally did arrive, a week had already passed since the incident. Castiel was still in the hospital and Dean Winchester was going insane. Ellen had approved a cell transfer for Sam and he now shared a cell with Crowley. At first he hated sleeping in Gabriel’s bed, which continued to smell like the dead Con-Artist for days after Sam moved in. He and Crowley were getting closer and they spent all their time together. Cain immediately jumped to the top of Dick Roman’s list of favorites and was soon made Mr. Roman’s second in command.

The first thing Dick Roman did was walk down to isolation by himself to pay a visit to Dean Winchester.

“So you must be the great Dean Winchester I’ve heard so much about,” he said, walking into Dean’s cell and leaning against the wall.

Dean glared at him but said nothing in response.

Dick Roman smiled and the sight made Dean’s flesh crawl. There was something very off about this new man and if Dean weren’t already in serious shit he would have tried to attack the smug bastard grinning down at him.

“You’ve probably never heard of me, my name is Dick Roman and I’m going to be taking over this prison until the stupid trench coat wearing warden finds his balls and is able to come back.” He laughed to himself and then walked slowly over to where Dean sat on his bed, “Although, you really fucked things up for him. According to Cain, you remember him right; salt and pepper hair with a brooding face, real hard ass, anyways, according to him you made Castiel your little bitch. Congratulations on the promotion, I’ve always enjoyed the chance to break the Head of a Mafia, the last one was so much fun but required a lot of leg work, but now I have the Head of the Italian Mafia sitting helpless in this cell!” Roman chuckled and he walked over and straddled Dean, threading his fingers into Dean’s hair.

“See, apparently at this jail, power comes with whomever you are able to make your bitch. You became the most powerful man in the jail that night with Mr. Novak, but I’m here and I will not have some lowlife convict be more feared then me just because the last warden was too weak to escape.” He sucked a hickey into Dean’s neck and then bit down hard enough to draw blood.

“Here’s what’s going to happen, first I’m going to make you my little bitch, then I am going to release you from solitary and parade you around the jail so that everyone can see that I own you.”

Dean could feel the tears spiking his eyes and found himself longing for Castiel. He thought about Cas as Roman removed is prison uniform, he remembered the way Castiel would try not to smile at something he said as Roman shoved into him without any preparation, he pictured Castiel’s blue eyes as pain took over the rest of his senses, he could hear Roman sucking more hickies into his neck and on his chest and he could feel himself being ripped open with every thrust but he did his best to block it out with memories of Castiel.

When Roman was finally done, Dean could feel the warm tears still sliding down his face. He could feel the blood and cum trickling out of his abused hole and down his ass and his legs, dripping onto the bed. When he opened his eyes, Dick Roman was gone and Dean’s uniform was resting in a messy pile on the floor. He knew he needed to get up and get dressed but he couldn’t move. Dean managed to cover himself up with a sheet before Garth came to check on him.

“Please…” mumbled Dean and Garth quickly unlocked the cell and awkwardly helped Dean dress and hobble to the infirmary.  Balthazar was in a rage when he saw Dean and he cursed under his breath while he did his best to patch Dean up.

“You’re staying in here for a few days, doctor’s orders,” Balthazar said, making a note on his clipboard and calling in a nurse. He handed her the piece of paper and told her that he would be out in a little while to finish signing the necessary paperwork for keeping Dean for longer than a day.

“Dean,” Balthazar said after the nurse had left, “I need to write that you were sexually assaulted on the report and I need to go into detail about the rape. Now, I know that Dick Roman is the one who did this to you; Garth said that he was the last person to visit you, but I need to know if there was anyone else there.”

Dean shook his head and felt the tears welling up again, he looked at the ceiling and tried to answer the rest of Balthazar’s questions to the best of his ability but he could only nod yes or mumble a “no”. By the time Balthazar’s questioning was over, Dean was crying again and just before the doctor left Dean whispered, “how’s Cas?”

Balthazar felt his heart rip in two. All this time, everything that had just happened and Dean’s main worry was how Castiel was doing.

“Cassie is doing much better, I’m going to visit him today. If you’d like I can bring him a message.”

Dean nodded, “can I have paper and a pen?”

Balthazar handed Dean his clipboard which had paper still on it, and then pulled out a pen from his pocket. “I’ll have to stay with you while you write it,” he apologized, “prisoner’s aren’t allowed to write letters without someone watching.”

Dean just nodded that he understood and Balthazar called the nurse in again and asked her to bring him the papers he needed to sign. The two men sat there for an hour, Dean writing his letter and Balthazar signing paperwork for various prisoners. Finally Dean unclipped the piece of paper and folded it into thirds; he wrote “Castiel” on the front and then handed it to Balthazar, along with the clipboard and pen.

The rest of the day passed slowly, every once in a while Balthazar would check up on Dean, but the prisoner never said anything other than the occasional request for water. A nurse had to force feed Dean but the meal was thrown up less than an hour after consumption and Balthazar was informed that Dean had developed a minor fever. Before leaving, he made sure that a nurse would be available to Dean all night long and that the infirmary doors were not only locked, but that a trusted guard stood watch overnight.

\---

The visit to Castiel was difficult. The warden was paler and thinner than the last time, his arm had not fully healed and according to the nurse on duty he was fighting an infection. She had quietly told Balthazar that surgery might be required.

“Hey Cassie,” Balthazar hummed as he walked into the room, a smile painted on his face.

“Balthazar,” Castiel murmured, his dim eyes locking onto Balthazar’s sad ones. “Why do you look so upset?”

Balthazar laughed lightly and sat down on the chair next to the hospital bed, “it hurts me to see you this way Cassie,” he sighed and Castiel smiled weakly.

“My sincerest apologies,” he said and Balthazar let out another huff of laughter.

“Not your fault dear. Just get better okay? We need you back at Folsom.”

“How is Dea- Dick Roman?” Castiel asked, pulling himself to a sitting position and resting his hands on his lap.

“A major fucking douche-bag,” Balthazar groaned, running his hand through his hair, “seriously Cassie, the guy has only been in charge for one day and already he’s fucking things up.”

 _Literally ‘fucking’…_ he thought.

Castiel shook his head in disappointment. “What a shame, I knew he had a bad reputation but I was hoping that his work would override his being a ‘douche-bag’.”

Balthazar laughed and shook his head in amusement, “If only, I swear the guy thinks that he’s untouchable.”

Castiel smiled and then became very quiet as looked down at his hands, “Uhm… How’s…”

Balthazar waited for him to finish the question, but he never did. “How’s Dean?” the doctor asked, looking at the warden carefully. The nod was tiny, but it was there.

“He’s doing… okay. He and Roman had a… uhm… well it’s kind of hard to explain. He did write you a letter though.”

Castiel’s head shot up and his eyes lit up a little.

 _Damn,_ Balthazar thought, _these two really have it bad for each other…_

“I have the letter with me, if you’d like it.” He offered, retrieving the letter from his bag and holding it out to Castiel who grabbed it with a muttered “thank you” and proceeded to shove it under his pillow.

“I’ll read it later,” he explained when Balthazar shot a raised eyebrow at him. “I do have a favor to ask you though,” he said hesitantly. “Will you keep an eye on Dean? I’m worried that Dick Roman may try and hurt him. From what I’ve heard, Roman isn’t the sort of man who would take kindly to a prisoner who tried to take advantage of a warden, and I have my reasons to believe that Dean didn’t try what he did because he wanted to.”

“What reasons?”

“Just… reasons…”

“Cassie.”

“Okay fine. Do you remember Gabriel Speight, the con-artist that Lucifer stabbed?”

“Of course I remember, it’s only been a week.”

“Only a week? It feels like a lifetime.” Castiel sighed, “anyways, his sister Naomi is my nurse. She told me that Lucifer was their cousin and that according to Gabriel, Lucifer was training Dean to take over the head of the Italian Mafia. She said that there is an extremely good possibility that before Lucifer died he could have threatened to kill Dean and Sam if Dean didn’t prove that he was worthy of taking over the mafia. She said that he would have probably given Dean some sort of task to prove this, such as-”

“Such as raping the warden,” Balthazar finished, processing the information. Castiel nodded and the two men sat in silence.

“I’m going to go talk to Dean and see what I can figure out.” Balthazar said after a while, standing up and putting his coat back on.

“Please do, tell him I will read his letter sometime tonight. And Balthazar,” Castiel said, “thank you for everything.”

Balthazar smiled and kissed Castiel’s forehead. “Get some sleep, and get better okay?”

“Okay.”


	14. Chapter 14

**Summary for the Chapter:**

> In which Naomi snoops and we figure out what the letter says.
> 
> Also in which Dean doesn't deny Balthazar suspicions.

Naomi stood over Castiel, who had fallen into a deep sleep after Balthazar left, and sighed. She noticed the folded piece of paper peeking out from under his pillow and checked over her shoulder before slipping it out and moving to sit down in the armchair by his bed. The paper was marked with Castiel’s name and she took a deep breath as she slowly unfolded it.

 

> _Dear Cas,_
> 
> _Balthazar said that you were in some kind of accident the night that… that night. I just wanted to write to see if you are doing okay and try to explain my behavior; I feel terrible…_
> 
> _When I first arrived at Folsom Prison and I met Alastair, he told me that he was going to “train me to take his place,” and by “his place” he meant that I was going to take over being the Mafia’s main inside man. Lucifer and Alastair were planning an escape that was supposed to take place in a month.  Part of their “training” included… well it included torture mainly… and sex… sometimes both at the same time. Before you wonder, I never reported it because, c’mon man, rape in a prison full of dudes is never taken seriously, and also because Lucifer was in a cell with my little brother, and no matter how much I hated my own situation, I could never put Sammy in a place where he might be killed if I can stop it._
> 
> _~~Back when we~~ Before we were caught, Sammy was never put in harm’s way. I was the one who did the killing and the torture and the kidnapping. He was in charge of staking out the place before hand and doing all the research. He never took up the blade, I never let him. He was never hurt, until the day we got caught and he decided to jump out of the car, guns at the ready, into the hands of all of the cops in Kansas._
> 
> _Then suddenly, he was sharing a cell with the head of the Italian Mafia and they were fuck buddies. His attitude began to get worse, and I could only bite my tongue and let Alastair do what he wanted with me, no matter how much I hated every second of it, because there is nothing I wouldn’t do for my little brother’s wellbeing._
> 
> _Then you stepped in. You started “punishing me” and as crazy as it sounds, those were the best times for me. I was away from Alastair, I got to see you, and even if you had made me scrub the bathrooms with a toothbrush (thanks for not doing that by the way) I would have still considered that to be the highlight of my day._
> 
> _The point is, Cas, you kind of saved me. You made me want to be a better man, to impress you. To show someone for the first time in my life that I could change if I wanted to, if I tried hard enough._
> 
> _On that day, when I killed Alistair and Lucifer… before I stabbed him Lucifer told me that if I wanted my brother and I to live, I had to prove that I was able to take his place as the head of the Italian Mafia._
> 
> _He told me that I had to rape you. Make you my bitch… he said that I had 24 hours._
> 
> _Then I stabbed him, and the countdown began. I wanted to warn you, to tell you that I had to do this, ask you to play along, but Cain was always there. I’ve spent enough time lurking in the shadows to realize when there is someone doing the same. He was there that night. I don’t know how much he saw, but my guess is that he left early because I was later informed that I am now the head of the Italian Mafia… Castiel, please help me. I can’t do this anymore._
> 
> _I know that this is an unfair request. I know that I don’t deserve anything from you. But I need you to know that I’m so sorry. I’m so sorry for everything that’s happened. I’m sorry it had to be your prison, I’m sorry that I was the one they chose to take over, I’m sorry that I couldn’t stop it. Cas, you put in a lot of time and effort to try and get me on the right path, and I was forced to repay you by acting like the monster I really don’t want to be._
> 
> _We need you back here Cas, I need you back here. Please tell me that I didn’t screw up too much this time. I never wanted to hurt you, and yet I still was able to land you in the hospital. I know I traumatized you, I hurt you Cas, just like I’ve hurt everyone else important to me._
> 
> _That day I killed Lucifer and he killed Gabriel, I hurt Sam. He lost two people to death that day and then I was sent to isolation (I don’t blame you for sending me there, and I’m not mad at you for following protocol, you did the right thing)._
> 
> _Balthazar is being really nice, I think he might see what you used to, I think he sees the part of me that wants to change, that wants to be better. Don’t worry about what happened between me and Dick Roman, I should have seen it coming, and I know that with Balthazar’s help, I’ll recover soon._
> 
> _I miss you Cas, and I know that I have no right to say that to you but it’s true. Please, get better and come back so that I can tell you all of this in person. Writing it out helps, but… words have never really been my thing. I don’t do apologies, I’ve never felt the need to say “I’m sorry” but dammit Cas, I am. I am so sorry. I hate what I did to you, I hate what happened between us that night. I just… I’m sorry Cas._
> 
> _Please get better soon, please don’t die because of me. I wouldn’t be able to handle it if I was the cause of your death… Please Castiel, get better._
> 
> _I’m so sorry._
> 
> _\- Dean Winchester_

Naomi let out a small sigh and looked back at the sleeping man in front of her. Castiel was snoring gently and he looked younger in the soft glow of the moon. She folded the paper back up and placed it back under Castiel’s pillow. He muttered something in his sleep and Naomi froze as he flopped over to face the other side. She remained very still and quiet and after a few minutes, Castiel muttered again.

“D-deeean”

Her eyes widened and she stared at her patient in wonder. After all of this, everything that had happened, after Dean had tried to rape him and inadvertently caused him to wind up in the hospital, barely clinging on to life, Castiel still clearly cared about him. So much so that he kept the letter under his pillow and muttered Dean’s name in his sleep.

Very quietly she made her way out of the hospital room, she grabbed her coat and purse and clocked out before walking out into the parking lot and getting in her car. She thought about Castiel and Dean, Sam and Lucifer and Alistair and the horrific events that had occurred at Folsom. She thought about Gabriel and how in love with Sam he was. How he would have done anything to keep the younger Winchester safe, and when push came to shove, he ended up doing exactly that. When she arrived at her house, she didn’t notice the car turning off it’s headlights just across the street, nor did she see the smaller man with curly hair sitting in the driver’s seat, watching her carefully.

\---

“Dean, listen to me, Dick Roman is on is way right now. I am going to give you something and it is going to make you feel much worse then you already are. He has to think that you are incredibly sick, otherwise he is going to try and use his authority to get you out of here and back into isolation where I can’t protect you. I’ve placed a waste basket on your right, you’re probably going to be throwing up a lot for a few hours… just try to aim for the waste basket,”  Balthazar’s usually calm British voice was tense and scared and Dean wearily opened his eyes to look at the doctor.

“Okay…” he whispered and Balthazar nodded before uncapping a syringe and plunging it into the crook of Dean’s arm. At first nothing happened, then all at once it hit him. Dean’s vision became blurry and his limbs felt as if they were being tethered down by giant weights. He tasted iron in his saliva and barely had time to roll over to his side before he began throwing up. It was only a few minutes later when he had been reduced to a shivering mess of limbs that he registered Balthazar’s hand gently rubbing his back.

The doctor let out a small sigh and then chuckled, “The waste basket is on your other right Dean.”

When Dick Roman entered the infirmary he immediately demanded to be taken to where Dean Winchester was. The nurse nodded quietly and led Roman and his men to the room. As soon as the door opened they were hit with the smell of vomit. Dick Roman’s face scrunched up in disgust and he glared at the pale prisoner lying helplessly in the bed. One of his men excused himself and ran towards the bathroom, his face already green. Balthazar was standing on Dean’s left, a mop in his hand and bucket of disinfectant at his feet, mopping up the mess Dean had just made.

“Hello darling,” Balthazar smirked when he saw the new Warden.

“You can call me Dick,” replied Roman, still glaring at Dean.

“Oh don’t worry, I already call you Dick, just not usually to your face,” the doctor responded smugly, leaning against the mop innocently, malice in his eyes.

Dick chuckled and turned his attention to Balthazar, taking his time to look the other man up and down. “I like a quick witted man Doctor Roche. You could be valuable to my team. I don’t often extend invitations such as this, I don’t enjoy outsiders very much, but I’m willing to make an exception for you.” He flashed a smile at Balthazar and then looked back at Dean, disapproval taking over his charming features. “Please notify me when he starts to get better. He may stay here until then, but I will be checking in on him regularly.”

“Of course, Dick. I will make sure to inform you when he is fully recovered.”

Dick Roman looked Balthazar up and down once more and flashed him another smile before turning around and striding out of the infirmary, head held high.

“He certainly lives up to his name,” Dean murmured weakly and Balthazar let out an amused laugh, looking over at his patient.

After a few weeks of Dick Roman paying Dean visits every day, and Balthazar feeding Dean medication to make him sick enough to warrant needing to stay in the infirmary, Balthazar had had enough. One morning he walked into Dean’s room and sat down next to his bed, letting out a sigh as he scanned the prisoners tired, sick body. Dean had lost a lot of weight and was very pale. He looked exhausted and it made Balthazar sad to see him in such a condition.

“We need to get you out of here…” the doctor said after a few minutes of silence.

“I’m not going anywhere without Sammy.”

Balthazar studied Dean’s face; Dean’s eyes were stern and his lips were pressed tightly together, his brow furrowed and for a minute, Bathazar was reminded what Dean Winchester was capable of.

“Of course we’ll get Sammy out too,” he said, nodding to himself and mentally going over everything they would need if they were going to try and make this work.

“Wait… are you serious?” Balthazar returned his gaze to Dean and was slightly taken aback by the shocked look on his face.

“Of course I’m serious Dean. It’s not safe for you here, and if it’s not safe for the head of the Italian Mafia, it’s absolutely not safe for his little brother. Besides, I have a feeling that if anything else ever happened to you in here and I could have done something to stop it, Castiel will kill me, bring me back to life and then kill me again,” he shrugged and cast a knowing grin at Dean who was trying to hide the fact that he was blushing. “You two really have it bad for each other.”

Dean’s eyes widened and he opened his mouth to protest, but shut it again when Balthazar winked and said, “no point in trying to hide it. He feels the same way you know, it’ll probably take a little while for you two to figure things out, but for right now, we need to start on an escape plan.”

Dean blushed again and then nodded slowly, studying Balthazar for any sign that he was lying. When he thought Balthazar wasn’t looking, he looked down at his hands and smiled to himself before suddenly throwing himself to the right and vomiting into the waste basket. 


	15. Chapter 15

**Summary for the Chapter:**

> In which we move forward and prisoners spew chunks. 
> 
> Also in which Balthazar isn't completely honest with his plans.

Sam sat on his bunk in silence. Crowley was watching him closely and as much as it was nice to have someone care about how he was doing, Sam really just wanted a few minutes to himself.

“Moose,” Crowley said, his voice a husky whisper, “talk to me Moose. I know we aren’t that close, you and I, but the thing is, we’ve both lost someone because of all this. You’ve lost a brother and a lover and I’ve lost a brother and a very good friend.”

Sam remained silent, glaring down at his hands. He heard his inmate sigh dramatically and he let out a sigh of his own and rolled his eyes. Crowley was making a lot of sense, but sense was not what Sam wanted right now. He wanted his brother back, he wanted Gabriel. It had been a month since ‘the incident’ as they called it. He had not seen or spoken to, or even heard from Dean in all that time and to say he was worried would be a serious understatement. No one seemed to know what had happened to Dean, or at least, no one was talking about it.

Crowley’s voice came from somewhere far away, “Hello dear, and who might you be?”

Sam looked up towards the door and saw a semi-familiar face. The man was quite attractive, but in a very snarky way. The look on his face was pure sass and Sam quirked a small smile as a predatory look took over the man’s face.

“The names Balthazar Roche,” the man said in a British accent that had just the hint of something else, “I’m the chief doctor in this hell-hole. I’m also the one who’s going to help break you out.”

Crowley squinted inquisitively and Sam felt his ‘bitchface’ fall effortlessly into place.

“And what in the world makes you think that we would be stupid enough to attempt that?” Crowley asked;* Sam noticed that even through his disbelief there was a glimmer of hope. Apparently Balthazar noticed too.

“Because if we can’t get you out, you’re all on the kill list. Starting with Dean,” the doctor retorted, raising an eyebrow and pressing his lips into a disapproving frown. “You know,” he continued, “I must say, this isn’t exactly the response I expected.”

“Why do you think my brother is in danger? He’s the head of the Italian mafia now, no one in here would dare lay a finger on him.”

“Not exactly ‘no-one’… none of the prisoners sure, but the new Warden has this thing about leaders of the Mafia, he can get very rough at times and he really likes to be on top… and I do mean that in every way possible. You’re brother was sent to the infirmary after his run in with Dick’s dick.”

Sam stood up, hands balled into fists, “What are you talking about?” he growled.

Balthazar raised his hands but held his gaze and held his ground. “I’m talking about Dick Roman making your brother his little bitch. I’ve been able to keep Dean safe since then. I have some medicine that if taken when not needed will make someone very sick for a few hours after taken. I’ve been making Dean take it in the morning so that whenever Roman comes in, Dean is too sick to be sent back to isolation; don’t worry your pretty head though, I know what I’m doing and it’s not going to damage Dean permanently. The point is, he’s safe for now. But there is only so long I can keep doing this before Dick starts to get suspicious. So I need to get you three out of here as soon as possible.”

Sam and Crowley exchanged looks before Sam turned back to the doctor. “Dean, he is okay though… other than the medicine you’re giving him to make him sick?”

“Yes, he’s still a bit shaken up and his body hasn’t fully recovered from the assault, but he’s doing much better than he was,” Balthazar looked down and shook his head sadly, “what happened, it never should have happened. I know why he did what he did to Cassie and while I’m not a fan of what happened, I understand why he did it.” He looked up at Sam again and locked eyes with the younger Winchester, suddenly very serious. “You should know that neither Cassie, nor myself blame Dean for what he did. And you need to listen to me very carefully Sam, what happened in that courtyard, what happened to Gabriel and Lucifer,* it’s not your fault. There is no way you could have known what was going to happen.”

Sam looked away, simultaneously biting back the urge to cry and the urge to punch Balthazar in the face. He felt Crowley lay a hand on his shoulder and instinctively leaned into the touch. After a minute of silence he sucked in a breath and shot a small smile at Crowley before turning back to Balthazar.

“So how are we going to do this?”

\---

Dean lay in his bed at the infirmary going over the plan Balthazar had told him about earlier that morning before going off in search of Sammy to relay the same plan to him.

There was a specific type of medicine, Baclofen, which when measured correctly would mimic death. Balthazar had explained that it was far from risk free but it was also the best way of getting Dean, Sam and Crowley out. Balthazar would give Sam and Crowley the same medicine Dean had been taking, once they were deemed sick enough to warrant being administered to the infirmary, he would start with Dean and work in intervals. Dean would be sent to the hospital under the guise that his condition had worsened, then after a few days there, Balthazar’s contact would administer the Baclofen, mimicking death and Dean would have to be transported to the morgue. Of course, he would never reach the morgue, another one of Balthazar’s contacts would be driving the car and take Dean to a safe house where he would be treated until he made a full recovery. The same would be done with Sam and Crowley and they would be free within a week of Dean’s escape. For safety measures, Balthazar was going to sneak the medicine to a few of the other patients, to make it appear that something was just going around.

The doctor had been making phone calls to his contacts all morning and the plan was set in motion as soon as he returned from talking to Sam and Crowley. He gave Dean a particularly strong dose of the medicine and Dean’s body reacted beautifully. Dick Roman had come in to check up on his favorite prisoner and had been greeted by the sight of the eldest Winchester a sweaty, shaky, pale and vomiting mess. Balthazar had also given another prisoner a dose of the medicine and pulled Roman to the side after he had seen both of the sick prisoners.

“They need to be sent to a hospital. I’m not sure what’s wrong with them, I’ve never seen anything like this before,” he lied, Dick Roman was uncomfortable with the idea but hesitantly agreed, not wanting to chance losing Dean, and the opportunity to torture him further, to something that could be fixed with the proper medication. The sooner Dean was better, the sooner he could be back under Roman’s control.

Dick missed the small nod Balthazar gave to the doctor who hooked Dean up to the IV in the ambulance, and he didn’t see the second injection the doctor made, which cause Dean to loose consciousness within seconds. The EKG went eratic before flatlining, and the door to the ambulance closed right as the doctor quickly grabbed the defibrillator and started to rub it together.

\---

Balthazar knew that the defibrillator wasn’t going to be used, he and Inias had studied together and knew what was happening. The look on Dick Roman’s face when he heard the flatline was like an early Christmas present. The stage had been set and now all that was left was to get Sam and Crowley out safely. Dean was on his way to the safe house where a John Doe was waiting to be taken to the morgue as the body of Dean Winchester.

He felt bad that he hadn’t warned Dean about the change in plans, but he had noticed Cain lurking around after he had spoken to Sam and Crowley and felt the need to step things up by a few days. If everything else worked out the way this had, the other two men would be out of here by the end of the week. All that was left was to make it seem like an outbreak instead of a break out.

Dick Roman stood in silence, his face contorted into a slight grimace as he watched the ambulance screech away. Balthazar clapped the warden’s shoulder.

“Don’t worry,” he said, “I’m sure Dean will be fine, it’s just a matter of getting the right treatment and then he’ll be back here in no time.”

Dick nodded, turned around and strode back into Folsom, still grimacing and very clearly agitated. Balthazar couldn’t help but smirk and congratulate himself on how brilliantly everything had gone. He returned to the infirmary and administered the medicine to two other patients before making his way to the kitchens.

Jane Tomassone was a very pretty woman, with curly dark red hair and bright green eyes; she was in her early thirties and had been best friends with Balthazar’s younger sister Hannah. After Hannah’s death when she was just ten, Jane and Balthazar lost contact until she was hired in Folsom as the resident chef. Balthazar considered Jane to be a very good friend and so he wasn’t at all surprised when she agreed to assist him with his plan, even though she knew she could get fired for it.

“So all I have to do is mix this in to a few of the water cups and that’s it?” She said, peering at the small bottle of Ipecac Balthazar had snuck to her.

“Yes, only two tablespoon are needed. Do not give anymore, and be prepared for a huge mess between 20 and 30 minutes later. Try and wait 15 minutes between giving it to someone. And only give it to the people on this list. If too many inmates become sick at one time, it will look more like food poisoning than a serious illness. I want you to also do this with two people tomorrow durning breakfast, one of them being Sam Winchester, and then one more person during lunch. Dinner tomorrow will have Fergus Crowley and two others on the sick list. We’ll need to administer it to one or two more people the next day, and one person the day after. Tomorrow evening when Inias comes to take away Sam and Crowley, he will bring an ‘antidote’ and we will have every prisoner drink it. This will explain why the outbreak ceased. Everyone infected will be sent to the hospital, and unfortunately we are going to need most of them to actually die if we are going to pull this off. Those other inmates will be given an injection either on the ride to the hospital or right before they are administered,” Balthazar explained, watching Jane’s face carefully to make sure that she understood. She nodded and cast him a smirk.

“You know Balth, it’s almost as if you’ve broken someone out of prison before.”

Balthazar laughed and winked, “I’ll never tell.”

\--------

That evening was a mess. Dick Roman was up to his heels in vomit, literally. He had gotten the call that Dean Winchester had died on the way to the hospital and was now at the morgue, waiting for instructions as to what to do with his body, when suddenly Cain rushed into the office.

“Sir, we have a situation in the cafeteria.”

The inmates were in frenzy, trying to push their way away from those who were spewing chunks all over the linoleum floors. The air was rancid and Dick gagged as soon as the harsh smell of vomit bombarded his nose. He covered his mouth and nose with his jacket and made his way over to the woman in charge of the kitchen.

“What the hell happened here?”

“I-I don’t know sir,” Jane stammered, her blue-green eyes wide in shock and horror, “some of the prisoners weren’t looking to well when they came in and then this started about half an hour into the meal! I know it wasn’t something that I cooked, otherwise everyone would be sick.”

Dick looked carefully at the people who were throwing up and quickly noticed a connection, all of those prisoners had been in the infirmary during the days that Dean Winchester and the other prisoner had fallen ill. He knew the infirmary log inside and out, having checked it every day to make sure that Dean hadn’t had any visitors.

He quickly made his way to the infirmary where he found Balthazar and his team running around prepping beds for the inmates who had fallen ill. They were all wearing facemasks and as soon as Balthazar saw Dick, he ran over and shoved a facemask into his hands.

“I don’t know what’s going around, but what I do know is that Alfie Johnston, the other prisoner who was infected at the same time as Mr. Winchester, died about an hour ago. Which at the time, made it two infected, two dead. For the safety of everyone in the prison, I highly suggest this infirmary be quarantined. At least until we can figure out how to cure it or how to stop it from spreading.”

Dick nodded solemnly in agreement. “If that is what you think will be best, then I will support that decision.” He quickly instructed that all the prisoners be returned to their cells before calling all of the prison staff into the conference room for an emergency meeting.

He stood behind the podium which was usually only used when important political officials came to give a speech, Cain stood off to his right and Balthazar stood at his left.

“In light of the recent outbreak, from this moment forward, any prisoner thought to be infected with, whatever this is, will be sent straight to the infirmary and into quarantine. Do not take any chances. We don’t know what early symptoms are and we have no idea how to stop this. If they look sick, they must be taken to the infirmary where Dr. Roche and his team will do their best to contain the outbreak until an antidote is found. Thank you.”

No one noticed the satisfied smirk Balthazar hid carefully behind a little cough, or the knowing wink Jane shot him a few seconds later.


	16. Chapter 16

**Summary for the Chapter:**

> In which Cas is an "Idjit", Dean escapes and a special someone returns.
> 
> Thanks again to my wonderful Beta Meg, without whom I guarantee this fic would be so much worse.

**Notes for the Chapter:**

> Oh my Chuck, I am so sorry for the long wait... I have this thing where I don't post a chapter until the next chapter has been sent in for editing and Chapter 17 took me for fudging ever to write! I've literally been working on it for the past two weeks! Again, I apologize. Hopefully we'll get back to a chapter a week, I want to have this fic completed by Thanksgiving... but I don't know how realistic that is. I do know however that we are reaching the end of this fic. I estimate maybe five or six more chapters (I already have the final chapter written)

“Castiel, wake up, it’s time to go,” Naomi said, shaking the still healing warden gently.

“Wha-where are we going?”

“You’ll see; I’m under strict orders not to explain anything until we get to a better place,” she said carefully removing his IV, “You’re just going to have to trust me on this okay? I’ve signed all the necessary papers to get you out, the only thing that’s left to do is actually walk out of here before Dr. Benton realizes that I’ve forged his signature and comes to check up on you.” She helped Castiel out of the bed and handed him his trench coat and started rushing towards the door, Castiel in tow.

“Naomi, wait,” Cas gasped just before his legs gave out beneath him and he toppled down gracelessly.

“Shit, wait right here I’ll be back in a minute,” she said, and with that she was gone.

“Don’t worry,” Cas sighed, “I’m not going anywhere…”

Naomi was soon back with a wheelchair which she helped Castiel get into before she was racing them both out of his room and down the hall.

“HOLD THE ELEVATOR!” she called, and a man who looked a lot like Sam looked up at her before reaching his hand in-between the closing doors and effectively stopping them.

“Thank you so much Dr. Wesson,” she smiled before turning her attentions back to making sure Castiel was still okay.

When they made it outside, a van was waiting. An African-American man rolled open the side door and helped Naomi lift Cas, wheelchair and all, into the back of the van.

“Take care of him,” Naomi said and the man nodded solemnly.

It wasn’t until the door had been closed and they were on the highway that the man finally introduced himself, “Name’s Rufus Turner, the old fart driving is Bobby Singer. We’re headin’ down to ol’ Singers Salvage where Mr. Dean Winchester will be arriving later on tonight. I have to tell you this, you’re already involved. No tryin to get out of this 'cause it just ain’t gunna work. This next week you’re gunna experience first hand how a real prison break works.”

As soon as Rufus said “Dean Winchester will be arriving later on tonight,” Castiel had stopped breathing. It was embarrassing how loudly his heart was beating and he could feel his cheeks and the back of his neck heat up significantly. He wasn’t sure what to make of the butterflies whipping up a storm in his stomach and for a moment he felt like he was going to pass out.

“Ya still with us?” A gruff voice barked from the front of the van.

Castiel nodded before realizing the man couldn’t see him, “yes, I’m still here,” he managed to whisper.

“Idjit.”

The man in the front seat was donned in a worn out baseball cap and a grey t-shirt with a longsleeve flannel rolled up almost to his elbows. He had a short beard and mustache and reddish brown hair that was beginning to grey. He looked tired and stern, but Cas could still see faint laugh lines hidden next to intelligent grey-blue eyes. He glanced at the warden and shot him a curious look.

“Tell me boy, what do you know about this plan?” he asked, and Castiel shook his head.

‘Nothing other than what Mr. Turner just told me,” he said quietly.

Rufus let out a harsh bark of laughter, “hear that? He called me ‘Mr. Turner’, like I’m some goddamn fed or something!”

“Can it Rufus,” Bobby growled.

The rest of the ride was spent in silence, and when they reached Singer’s Salvage a few hours later Castiel had regained the power to move his legs and was more than happy to be out of the stuffy van.

When they walked into Bobby’s house, the warden was shocked by how much stuff was there. The living room was full of old books, there was a fireplace on the far wall and a large desk directly in front of it. The window had strange symbols painted in red on it and there was a man sleeping on the worn out couch. Castiel only had a moment to take it all in before Bobby herded him upstairs and showed him to his room.

“This is where you’ll be staying,” he explained with a huff, “I put some of Dean’s clothes into the closet for you to use, he’s got more in his room so don’t worry about him needing stuff when he gets here. Rufus and I will be downstairs if you need us. The bathroom is just down the hall and to the right. There’s a new toothbrush on the counter for you, toothpaste is in the drawer and feel free to use whatever else you need. Washcloths are in a basket under the sink. There’s a towel on your bed.”

With that he turned around and walked out of the bed room, shutting the door behind him.

The first thing that Castiel did was grab a pair of sweatpants and a t-shirt, along with his towel and a pair of thick socks and pad down the hallway in search of a shower. The water was perfect, just the right temperature and pressure and when he got out, he felt refreshed. His mind wandered to the muffled voices wafting up from downstairs as he dried off and got dressed. The two gruff voices of the men who had brought him here were now joined by a third, vaguely familiar voice, and Castiel decided that the man who had been sleeping on the couch must have woken up. He made his way to his bedroom and sank down onto the twin sized mattress and drew the soft blanket up to his chin, allowing sleep to take over.

 

\---

 

Dean woke up dazed and confused, with a paramedic smiling down at him.

“What the fuck…” he muttered, immediately regretting the decision to speak and breaking into a series of coughs that scraped his dry throat.

The paramedic chucked and checked Dean’s vitals before helping him sit up and offering him a bottle of water.

“You had us worried there; you were out a lot longer then we’d planned for. It’s been two hours. We’re almost to our destination. You’re a free man Mr. Winchester,” the paramedic said, sitting back and taking out his phone. Dean watched as he dialed a number and put the cell phone to his ear.

“Hey Balthazar, it’s Inias. Dean’s awake and his vitals are fine. We’re about thirty minutes away from Bobby’s. … He’s already there? Okay good to know. … No I haven’t . … Make’s sense, how are things in the prison? … God I would have paid good money to be there when Dick heard! So everyone thinks that both of them are dead correct? … Yes the John Doe arrived in a different ambulance. According to the hospital, Malachi was the paramedic who was responding to the call from Folsom, there will be no suspicion when he’s the one who shows up with the body. Also, I talked to Tessa, the Mortician, and she’s on board. She’s going to log the corpse in as Dean Winchester and she knows what symptoms to say were the causes of death. The John Doe will be cremated in the morning, effectively ending the life of Dean Winchester. Tessa already has the Death Certificate ready and should have already signed it. … Tomorrow? … Both of them? Okay, we’ll prepare for those corpses as well, and I’ll notify Tessa and Malachi. … Yes I’ll tell Bobby and Rufus as soon as we see them.  … okay, see you tomorrow Balthazar. I’ll call you when we reach Singer’s.”

Inias ended the call and returned the cell to his pocket.

“Bobby Singer?” Dean said curiously.

“Yeah, he owns Singer’s Salvage in-”

“I know what he owns, he was an old friend of my dad’s; Bobby was more of a father to me then my father ever was. I wasn’t aware that Balthazar knew him.”

“Bobby helped Balthazar get back on the right track years ago, he’s actually the one who encouraged Balthazar to go to medical school. When Balthazar was about 13, he got into drugs and prostituted himself in order to pay for his addiction. One night, one of his Johns decided that he wanted it rough, and for free. He forced himself of Balthazar and then beat him near senseless when he had finished. Bobby found Balthazar in an ally, completely naked and hiding behind a dumpster. He took Balthazar home and cared for him, helped him get clean and educated, even gave him a job at the yard.”

Dean sat there in silence, _that explains why he was so upset by what Roman did…_ he thought, remembering how outraged the doctor had been when he had stumbled through the infirmary doors clutching onto Garth for support. The rest of the ride consisted of Inias asking Dean a few questions and Dean answering as best as he could without feeling like he was going to puke. When they pulled up to Bobby’s house, he was flooded with memories and couldn’t keep back the smile that spread across his face. Bobby was waiting on the porch along with Rufus and when Dean reached them, Bobby pulled him into a crushing hug.

“Good to see ya again boy,” he said. Dean wrapped his arms around the man and felt tears well up.

“Good to see you too Bobby,” he said, holding on to Bobby and burring his face in the older man’s shoulder. When he pulled away, he was pleased to notice that he wasn’t the only one who had teared up at the reunion as Bobby wiped his eyes.

Rufus walked over and clapped him on the shoulder, “Glad you’re okay Dean, your friends were worried.” Dean smiled and looked around for Castiel. His gaze landed on a figure standing in the doorway.

“Hey there Dean-o, welcome to the land of the free!”

Dean’s mouth dropped as the man walked out onto the porch, a playful smirk spread across his lips, golden eyes gleaming mischievously.

“Gabriel?”

 

\---

 

Castiel woke up to the sound of a vehicle driving over the gravel in the front. He listened to the car doors open and people walk up to the house. The voices were barely audible but he thought he heard someone say Dean’s name and he shot up from the bed.

 _Dean’s here,_ he thought, both excited and nervous. _He made it out okay! He’s safe._

Castiel grinned as he made his was quickly out of the room and down the stairs, but his smile faded when he saw the figure by the front door. The man hadn’t seen or heard Castiel and when he spoke, it was directed at the men outside.

“Hey there Dean-o,” Gabriel said, “welcome to the land of the free!”

Castiel stood rooted in shock, “Impossible…” he muttered as he watched the golden haired man open the door and saunter onto the porch. He heard Dean’s surprised voice call out the con-man’s name in confusion and slowly Cas made his way outside where he found Gabriel smirking at a very tired, very sick Dean Winchester. Bobby and Rufus were smiling and there were two paramedics who looked vaguely familiar. It took him a minute to realize that he had seen them talking to Naomi on several occasions. He heard Dean breathe in a quiet gasp and when he looked at the escapee, he felt his chest seize up. A smile spread over his face and he let out a small sigh of his own before walking over to where Dean stood.

“Dean…” he began, but the taller man silenced him by pulling him close and pressing their lips together in a soft embrace. Castiel didn’t respond for a moment and Dean pulled away, worriedly gazing into Cas’ eyes. Cas realized that Dean was nervous and he nodded slightly before wrapping his arms around Dean’s neck and pulling him back in, closing the gap between them once more and kissing him gently. He smirked when he felt Dean melt into the kiss and hold onto him tighter. Cas felt his breath escape him and he carded his fingers through Dean’s hair, savoring the softness of the man he had fallen for. Dean moaned at the sensation and ran his hands up and down the wardens back, feeling the muscles hidden under the thin t-shirt.

The moment was cut short by a loud, “Well FINALLY” which was supplied graciously by Gabriel, who was standing much closer than necessary. Bobby cuffed the con-artist upside his head and shooed him back inside, along with Rufus, who seemed to be having difficulty comprehending that Dean Winchester had just kissed another man. Dean kept his arm wrapped firmly around Castiel’s waist as they said farewell to the paramedics, thanking them for everything and confirming the next day’s plans.

Tomorrow would bring Dean’s first day as a free man, and it would also bring Sam Winchester and Fergus Crowley safely out of Dick Roman’s clutches. Dean and Cas didn’t speak as they made their way upstairs, ignoring everyone else, favoring some privacy over socialization. There would be time for chatting later. For now, all either of them wanted to do was curl up in bed together and spend some time getting to know each other without any Warden/Prisoner boundaries to get in the way. Tonight they were just Dean Winchester and Castiel Novak, two men who through and insane set of circumstances, beat the odds and found love in the worst place in America.

 

\---

 

Gabriel and Bobby sat on the couch, clutching beers and talking quietly as to not disturb the couple who had disappeared upstairs as soon as the paramedics had.

“So,” Bobby said, looking at Gabriel carefully, “Sam’s arriving tomorrow. How are you feeling about that?”

Gabriel avoided the older man’s gaze and prayed that it was dark enough Bobby wasn’t able to see the blush that had creeped over his cheeks. He heard Bobby let out a gruff chuckle at the sight, but when he looked up, there was no sign of teasing in the older man’s face; just a soft understanding that Gabriel had never been on the receiving side of.

“I’m a little nervous, no one in Folsom knew about my escape except for Balthazar who suggested it… I have no idea what I put Sam through, or even Crowley for that sake. Everyone was informed that I was killed by Lucifer, Sam has spent the last month under the impression that I died, add the fact that Dean killed Luci and then was sent to solitary, means that Sam had to sort through all of that by himself,” Gabriel sighed and ran his hands over his face and through his hair, heaving a sigh before looking sadly at a small stain on the carpet, refusing to meet Bobby’s gaze.

Bobby watched the man sitting opposite him carefully. They had both made a point not to mention Sam during the time Gabriel had been living with him, which started the day of the con-artist’s supposed death, but times were changing and Sam would be arriving tomorrow, accompanied by Crowley. Dean and Castiel had taken the surprise of Gabriel’s survival better than expected, but everyone knew that the two men had other things to think about than a con-artist who had cheated death.

After a long while of silence, Gabriel allowed his eyes to meet Bobby’s, the older man cast him a small smile and leaned over, patting Gabe on the shoulder gently.

“Listen here boy, Sam Winchester is no fool, but he is a damn princess. Now, there ain’t a doubt in my mind that he’s going to be overjoyed that you’re alive, but unlike with Dean and Castiel, it’s not gunna be all rose tinted glasses and longing gazes that will rot your teeth if you look too long. I’ll bet my own soul that Sam is gunna be pissed as hell when he finds out that you’ve been alive this whole time. He’ll come 'round eventually,” Bobby added when he saw Gabriel’s face fall, “from what I’ve heard from Balthazar, you’ve got Sammy wrapped around your little finger. Of all the people he’s lost, you’re in the top five of people he misses most. Right up there with his mother and Dean.”

“And Lucifer…” Gabe muttered to himself, earning the mother of all bitch faces from Bobby.

“I don’t know much about what happened there, but from what I can tell, that particular relationship wasn’t much of a choice. You were, he chose you and when you died, he chose to change into your cell.”

Gabriel’s head shot up in surprise, a pleased look hidden in his golden eyes and his lips twitching up into a small smile. Bobby rolled his eyes, but Gabriel noticed that he too had a smile trying to escape.

“Idjit,” the older man muttered and Gabriel chuckled.

“I’m gunna head to bed old man. I’ll be needing all of my energy if I’m going to make it through tomorrow,” he stood up and stretched before winking salaciously at Bobby, “who knows, if things go well I might even need some extra energy for tomorrow night between the sheets.” Gabriel laughed and ducked, the book that Bobby threw barely missing his head. He sprinted upstairs still laughing and made his way to the room he had been using. 


	17. Chapter 17

**Summary for the Chapter:**

> In which Dean and Cas FINALLY do the do.

Castiel’s cheeks were starting to get sore from smiling so much. Dean had held on to him all night, and as they made their way upstairs their hands were still entwined, smiles gracing both their faces. Dean led Cas to a room further down the hall from where the other man had slept last night. The Winchester stopped, hand on the knob and gazed into the piercing blue eyes of the man smiling lovingly at him.

Cas knew what was happening. Dean was giving him a way out, the right time to say goodnight and walk back to his own room. A warmth consumed him and for some unfathomable reason, when he stared into the forest green eyes of his almost lover, he felt grounded, secure, like he finally had found a home. He slowly moved his hand to rest over Deans and together they turned the knob, eyes never leaving each other as they crossed the threshold.

The room was bigger than the one Castiel had slept in, and so was the bed. There was an old record player in the corner and to its right, three shelves were stuffed with various vinyls. On its left, the wall had been made into a giant book shelf which held a sizable collection of works that immediately piqued Castiel’s interest. He looked from Dean to the books and then back again, silently asking permission to investigate. Dean smiled and walked over to the record player as Castiel ran his fingers along the spines of the worn out books. It was clear that each book on the shelf was well-loved and had been read several times. He quietly catalogued each book in Dean’s collection, smiling whenever he found a book that he knew was resting on his bookshelf back at home.  Out of the corner of his eye he watched Dean select a record and place it gently on the player, resting the needle along the rim of the vinyl and smile to himself as the music trickled out of the speakers which hung on the walls.

Castiel turned and smiled at Dean who grinned back.

_There are places I remember,_

_All my life though some have changed,_

_Some forever not for better_

_Some have gone, and some remain,_

Dean extended a hand to Cas, who looked at it for a moment before slipping his own hand into Dean’s firm grasp, allowing himself to be pulled in. He chuckled as Dean pulled him close and wrapped one arm around his waist and began to sway.

_All these places have their moments,_

_With lovers and friends I still can recall,_

_Some are dead and some are living,_

_In my life, I’ve loved them all,_

Dean pulled away, looking into Castiel’s eyes as he started to sing along with the gentle music, still holding the warden close.

_But of all these friends and lovers,_

_There is no one compares to you,_

_And these memories lose their meaning,_

_When I think of love as something new,_

They stopped moving and Castiel pulled them gently over to the bed, shuffling to rest his head on the pillows, allowing Dean to crawl over him. Castiel wrapped his arms around Dean’s neck, ran his fingers through the other man’s hair as Dean continued to sing.

_Though I know I’ll never lose affection,_

_For people and things that went before,_

_I know I’ll often stop and think about them,_

_Dean leaned down and ghosted his lips over Castiel’s,_

_In my life,_

_I love you more._

Cas lifted his head and their lips met; he pressed them together for a moment before Dean started kissing with more and more passion. Castiel groaned into the feeling of Dean’s soft lips against his and when Dean’s tongue peeked out and swiped gently across the seam of Castiel’s lips in a silent plea, Cas parted them willingly and groaned again as Dean’s tongue started exploring and claiming his mouth with such attention and worship, it felt as if they were melting into each other. Cas tightened his grip in Dean’s hair, drawing out a moan which Castiel eagerly devoured, pulling Dean’s hair again and pressing one of his hands on Dean’s lower back, guiding him down. Dean let out a small gasp when Castiel wrapped his legs around the Winchester’s waist and he ground gently down, gyrating his hips and shuddering when he felt their erections press together.

Beneath him, Castiel moaned and arched into the feeling, pressing himself closer to Dean. Dean was confused when Cas pulled away irritated and looked him in the eyes.

“Too many layers,” gasped the warden, his blue eyes becoming black with lust.

Dean chucked and nodded in agreement, quickly shedding his flannel and pulling his black undershirt off in one fluid motion.

Castiel stared, taking in the golden glow of Dean’s torso. Dean’s muscles were clearly defined, a small V dipped down, hiding behind the annoying fabric of the jean’s that hugged Dean’s ass in all the right ways. Cas ran his hands softly over Dean’s chest, tracing over every dip and curve. Dean moaned and his head fell back as Cas mapped out his body. With a quick movement, Cas flipped them over so that Dean was the one laying on his back, staring up at Castiel with wide eyes. Cas sat up and continued exploring the man below him. He traced the tattoo that covered Dean’s heart; at first he thought it was a sun, but upon examination he realized that it was a star inside a circle inside a ring of flames. He looked questioningly at Dean whose eyes had closed again. Cas chuckled when Dean’s glared at him upon realizing that Cas had stopped. Castiel tapped Dean’s tattoo and tilted his head to the side, Dean raised his hands to cup the warden’s face and pull him into a kiss.

“I’ll tell you about it tomorrow,” he muttered, “but for right now, I would really love it if you would please fuck me.”

Cas pulled away and smiled wolfishly down at Dean, “I’ll see what can be arranged,” he growled before yanking his own shirt from his body. He got off of Dean and stood up on the bed.

“Pants. Off. Now.” He commanded and Dean’s breath hitched. In Dean’s haste to obey he ended up rolling off the bed with a loud *thunk* and Castiel laughed and helped him back up.

“You okay?”

“Just a bruised ego, that’s all,” Dean grimaced, a blush creeping on his face, making his freckles stand out even more.

“So you’re not hurt,” Castiel asked, and when Dean shook his head Cas’ face turned stoic, “then tell me Dean Winchester, why the fuck are your pants still on?”

Dean fell onto the bed dramatically and whimpered, “Cas, I’m in paaaaaain, I don’t think I can take my pants off by myself, it huuuuuuurts.” Castiel tried and failed to bite back laughter and he moved, completely naked, to stand in between Dean’s legs.

“Don’t worry baby,” he murmured, “I’ll take care of you.” He made quick work of discarding Dean’s jeans but decided to take his time with the removal of the thin batman boxers. He toyed with the waistband and earned a hiss of pleasure/pain when he pulled on it and allowed it to snap back into place. Dean glared at him, but there wasn’t any heat behind it and Castiel smirked, making sure Dean was watching as he took the waistband in-between his teeth and started to pull it down.

Dean let out a guttural moan at the sight, lust ridden green eyes locked with mischievous blue ones and Castiel finished removing the boxers with his hands as he took Dean’s erection into his mouth.

Dean stopped breathing as he felt Castiel’s tongue flick his slit, tasting the cum that was leaking from it. When Cas started to tease the seam of Dean’s lips with his fingers, Dean quickly pulled them in, sucking and licking them. Cas took his time licking and kissing and tasting and humming, figuring out what Dean liked, what pulled the best noises from between the escapee’s lips.

“C-Cas…” Dean groaned around the warden’s fingers when he felt a heat curling in his stomach. Castiel was quick and he gently pinched the base of Dean’s erection, effectively holding the orgasm at bay for a little while longer. He pulled his spit slick fingers from Dean’s mouth and moved them down to tease Dean’s hole. He felt the muscled tighten as Dean shivered in anticipation. He pulled away and Dean moaned pleadingly;* Castiel took a moment to admire the man splayed out on the bed before him.

Dean’s body glistened with a thin layer of sweat, he was shaking and his eyes were shut. His mouth hung slightly agape and his cheeks were flushed with arousal. Cas’ gaze wandered down resting on Dean’s erection. He noted that Dean was about the same size as he was, but a little thicker and a little shorter. It curved beautifully upwards, leaking cum onto Dean’s stomach, Cas absentmindedly swirled his finger in the milky fluid and Dean’s eyes shot open. Cas met his gaze and smirked as he brought cum coated finger to his lips and slowly licked it clean. Dean groaned and surged forward, pulling their mouths together in a heated embrace. Castiel indulged him for a few minutes before he pulled away and pushed Dean back down.

“Dean, where do you keep the lube?”

Dean started up at him blankly for a moment before pointing weakly at the bedside table on the left side of the bed.

“Don’t move,” Castiel commanded before making his way to retrieve the lube and a condom from he drawer. When he moved back he gently prodded Dean to roll over. Dean obliged and got on all fours, lifting his ass in the air and shaking it tauntingly at the warden who rolled his eyes and bit back a moan. He uncapped the lube and applied a generous amount to his fingers and gently traced Dean’s hole, massaging the ring of muscles, getting them to relax before he slid his index finger deep inside Dean. He felt the muscles tighten around him and he stroked Dean’s lower back, soothing the other man before he started moving his finger in and out, circling it gently inside Dean getting him ready for the second finger.

“Cas… please…” Dean gasped and Castiel slowly slid a second finger in with the first. He let Dean adjust again before he began scissoring him open. Dean’s breath was ragged and he started to thrust backwards, fucking himself on Castiel’s fingers. When Cas brushed against Dean’s prostate the reaction was immediate;* Dean’s back arched and he let out a small scream of pleasure, followed by panting and thrusting back harder in a desperate attempt to have Cas hit that sweet spot again. By now Cas had three fingers working easily in and out of Dean and when he pulled them out Dean sobbed at the loss. Cas squeezed the base of his erection to keep him from coming when Dean let out a wonton moan. He hissed as he applied the cool lube on himself, and smirked as he squirted some directly from the bottle into the crevasse of Dean’s ass, earning a cry from the shaking man. 

“Caaaaassss….. please baby,” Dean gasped, wiggling his hips back inviting Castiel to take him. Castiel took a deep breath and rubbed a calming hand on Dean’s lower back, moving his hands down lovingly to massage Dean’s cheeks, spreading them apart and leaning down to press a kiss to his tight hole. Dean let out a yelp when Castiel suddenly thrust his tongue inside and ate him out. Then the sweet slickness of Cas’ tongue was gone and Dean’s eyes fluttered shut again in anticipation.

The record had stopped playing music, and much to Dean’s dismay Castiel removed himself completely from the bed and walked over to the shelf of vinyls. Dean whimpered and his legs shook as he watched Castiel bend over to examine the records. Castiel shook his ass at Dean and looked over his shoulder, his blue eyes bright, bottom lip trapped in between his teeth seductively. Castiel stood up slowly, making sure that Dean watched the whole thing. He replaced the Beatles record with the one he had chosen and turned back towards Dean as the music began to play.

_Here come old flattop, he come grooving up slowly_

_He got joo-joo eyeball, he one holy roller_

_He got hair down to his knee_

_Got to be a joker he just to what he please,_

Dean whined as Castiel sauntered towards him, wiggling his hips, his cock erect and dripping onto the carpet as he made his way towards the trembling man on the bed.

“Really Cas?” Dean groaned, a smile playing at the corner of his lips as the warden tauntingly swayed in front of him just  out of Dean’s reach. Castiel laughed and Dean decided that it was one of the most beautiful sounds he’d ever heard, with one quick motion he shot up and grabbed Cas’ arm and pulled him down onto the bed, smirking when the blue eyed man yelped in surprise. He watched Castiel’s eyes narrow in mock malice and the low growl that emitted from his lips was sinful and Dean found himself surging forward to once again take claim of the sinful mouth of the man below him. Castiel hummed in approval of the Winchester’s tactics and wrapped his arms around the escapee’s neck, pulling him closer. Dean allowed himself to be pulled down and enjoy the blissful feeling of skin on skin.

_He wear no shoeshine, he got toe-jam football_

_He got monkey finger, he shoot coca-cola_

“Dean,” Castiel said calmly as he pulled away, “Dean, I would very much like to fuck you right about now.”

Dean stared for a moment and inwardly cursed the warden for seeming so calm. Dean winked at the dark haired man, “As much as I would love that angel, you’ve got me in the playing mood.” He smiled innocently before planting a kiss on the pair of flushed, slightly chapped lips that graced the warden’s face. Castiel’s eyes widened as he watched Dean move slowly down, kissing and licking every inch of the warden’s slim torso. Dean nipped Cas’ nipple and savored the guttural moan Cas let slip at the sensation.

_He say, “I know you and you know me”_

_One thing I can tell you is you got to be free_

_Come together_

_Right now_

_Over me_

Slowly, torturously, Dean broke Castiel apart piece by piece. It was only once Castiel was in an equal state of neediness that Dean pulled away and whispered into Castiel’s ear, “Castiel, you may fuck me now.”

Dean’s eyes widened in surprise at the speed in which the warden flipped them over, he barely registered the sound of the condom foil ripping before he felt the blunt head of Castiel’s erection pressing against his hole. He shivered and closed his eyes, focusing all his attention on feeling what was about to happen.

_He roller coaster, he got early warning_

_He got muddy water, he one mojo filter_

Dean peeked through lidded eyes at the man above him who had stopped moving and was patiently waiting to lock eyes before continuing.

_He said, “one and one and one is three”_

_Got to be good-looking cos he’s so hard to see_

“Cas,” Dean started to complain, but he quickly lost his train of thought when in one fluid motion Castiel bottomed out.

_Come together_

_Right now_

Both men groaned and panted, fighting for control of themselves, gulping in deep breaths trying to calm down, neither wanting to come to soon.

_Over me._

“Move,” Dean moaned and Castiel willingly obliged, moving his hips in lazy circles.

_Come together_

“Cas,” Dean pleaded, praying that the warden would take the hint and pick up the pace.

_Yeah come together_

Cas began to slowly move in and out, bringing himself to the verge of pulling completely out and then pushing himself back in at what seemed like a snail’s pace.

_Yeah come together_

Dean was done with the teasing, “Castiel Novak, if you don’t start fucking me like you mean it then so help me God, I swear I will flip us over and tie you to the head post and ride your cock until you can’t see straight.” This earned a challenging smirk from the blue eyed warden and much to Dean’s mortification; Castiel came to a complete stop, sheathed fully inside Dean.

_Yeah come together_

Dean could feel Castiel’s erection pulsing inside him, and he locked eyes with the infuriating man above him and shot a smug smile at him before purposefully tensing up around the blue-eyed man.

_Yeah come together_

Castiel gasped and his head fell back. Dean let out a chuckle and was quickly silenced when Castiel growled and started pounding into him, hard and fast. Each thrust rocked Dean to his core and he clawed at Cas’ back, the need to somehow be closer overtaking his senses.

_Yeah come together_

Castiel shook at the tightness of Dean, at the feeling of Dean’s fingernails assaulting his back, at the feeling of skin against skin, the hardness of Dean’s erection trapped between them. Cas gasped as Dean tightened around him again and he gently nipped the Winchester’s neck, snaking a hand between them and taking a hold of Dean’s erection, jacking him off in time with each thrust, earning a loud groan of pleasure in response. He felt one of Dean’s hands move up the nape of his neck, pulling gently at the soft dark hair. Castiel sucked a dark circle on Dean’s neck and then sucked another one on his collarbone, continuing to thrust deeply inside the panting man below him.

_Yeah come together_

The headboard smacked mercilessly against the wall in time with Castiel’s thrusts. Castiel began to chant Dean’s name over and over again as he pounded with everything he had, earning a litany of broken praises from the escapee.

_Yeah, oh_

_Come together_

Castiel felt a heat pool in his gut and yelled Dean’s name as he came deep inside the Winchester. Dean shuddered and cried out a broken “C-CAS” as his own orgasm broke free. Castiel thrust a few more times and continued jacking Dean off, riding them both through their orgasms.

The record player had gone silent again and they lay in near silence, the sound of heavy breathing and their hearts pounding against their chests filling the room. Castiel slipped out of Dean and shakily stood, making it only far enough to grab a t-shirt from the floor and returning to gently clean them up, the soft fabric feeling rough against his tender member. Dean whined at the feeling and Castiel placed a gentle kiss on Dean’s cock and smiled at the lazy grin that spread across the other man’s face.

“C’mere,” Dean said, reaching out to pull Castiel close. Cas tossed the shirt unceremoniously onto the ground, walked over to flick off the lights before he made his way back to the bend and crawled in, tangling himself around Dean. He rested his head on Dean’s chest and listened to the escapee’s heart beat slow to a lulling rhythm. His eyes drifted closed and he smiled when he felt Dean place a tender kiss on the top of his head. He snuggled closer and his smile widened when Dean wrapped his arms tighter around Cas’ torso, drawing him as close as possible and humming in contentedness.

“Hey Cas,” Dean whispered in the darkness.

“Yes Dean?”

“I’m sorry.”

Castiel held onto Dean tighter and leaned his head up to kiss his jaw, “I know Dean, I forgive you. And I want you to know that I don’t blame you for what happened; it’s not your fault that I got into that accident.”

“But-”

“Dean Winchester, you listen to me,” Castiel said, moving to turn on the lamp on the bedside table and looking Dean in the eye. “It’s not your fault. I know why you did what you did and I forgave you a long time ago. If I hadn’t do you really think I would have made love to you tonight?”

Dean looked surprised and Castiel leaned down to kiss him chastely. When he pulled away he noticed the tears welling up in Dean’s eyes and he carded his fingers lovingly through Dean’s hair.

“Dean, what’s wrong?”

“I- I just… I don’t understand how you’re not mad at me. I- I tried to rape you Cas… I shoved you against the wall and-”

“I know what happened Dean, I was there,” Castiel smiled gently and cupped Dean’s face, “Dean, what happened isn’t your fault.”

“Cas,”

“I want to hear you say it. Tell me that it wasn’t your fault.”

Dean looked away from the piercing blue eyes of his lover, “I can’t…”

“Dean. Say it. ‘It wasn’t my fault’.”

A tear fell from Dean’s eye and he shuddered when Castiel kissed it away.

“Dean…”

“It wasn’t my fault,” Dean muttered halfheartedly, still refusing to look Castiel in the eye.

Castiel kissed him, “say it again,” he whispered, his breath ghosting across Dean’s lips.

Tears now flowed from Dean’s eyes and he sucked in a shaky breath, “It wasn’t my fault…” he said, still not convinced.

Castiel kissed him again, “again,” he commanded and Dean let out a small sob.

“It wasn’t my fault.”

Cas kissed his nose, “again.”

Dean was shaking now, hot tears cascading down his face and dripping onto the bed. “It wasn’t my fault. It wasn’t my fault.”

Castiel kissed his eyelids, “it wasn’t your fault Dean.”

“It wasn’t my fault,” Dean sobbed pulling Cas closer and holding onto him for dear life, “I didn’t want to… they were going to hurt Sammy, oh god Cas! I didn’t want to hurt you! Lucifer told me… Dammit Castiel I’m so sorry! He knew you were the one thing in that godforsaken place that made me happy and he wanted to take you away, I thought he had succeeded! Cas I hated myself for hurting you, and when Balthazar said you were in the hospital... I thought you were going to die and… I just…” Dean clutched onto Cas and his body shook as he sobbed into Castiel’s shoulder.

“Dean, it’s going to be okay. It’s not your fault,” Cas whispered, rolling them over so that Dean rested partly on top of him, “I don’t blame you, it’s not your fault. I’m okay, you’re okay.” Dean continued to sob as Castiel pressed his nose into Dean’s hair, inhaling his scent.

“Dean, we’re okay. We’re going to be okay. I love you.”

Dean let out a broken wail into Castiel’s neck and pressed himself closer. Castiel held Dean tight, reaching over to turn the light off and absentmindedly rubbing Dean’s back. After a while Dean started to calm down, quiet hiccups shook his body every once in a while.

“Cas?” Dean said after some time.

“Mhm?”

“Did you mean it?”

“Did I mean what Dean?”

Dean took a deep breath and Castiel pulled him closer.

“When you said you love me… did you mean it?”

Cas smiled and gave him a gentle squeeze. “With all my heart.”

Dean was silent for a while and Castiel had begun to think he had fallen asleep when he heard Dean’s voice, barely a whisper against his skin,

“I love you to, Cas.”

Castiel planted a kiss on Dean’s head and they both allowed sleep to wash over them, wrapped up in each other’s embrace, smiles spread on their faces. 


	18. Chapter 18

**Summary for the Chapter:**

> In which the Moose escapes, Crowley falls in love, and a special reunion doesn't go quite as well as people hoped.
> 
> ____________________________________________________________________________________  
> /\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\/\   
> \-------------------------------------------------------------------------
> 
> I know, I know, another 10 day wait... I'm so sorry. Meg and I have been really lazy lately... but whatever. Also, sorry this is a shorter one. The next one is rather long so it makes up for it. I think I want to try to have a new chapter out every Tuesday. We'll see what happens. Please leave your comments. I love it when you guys write to me :) 
> 
> Come join us on Instagram!!  
> Maddie (Author): @/Candy.Cane.Castiel  
> Meg (Beta): @/MiniChocolateMoose

The day after Dean’s “death” proved to be highly disgusting. Balthazar had decided last minute to go the full ten yards with the sickness running around and after breakfast there were several cases of prisoners puking their guts out. Others prisoners were struck suddenly with a high fever and among those laying helplessly in the infirmary beds was Fergus Crowley, who had taken to shooting a searing glare at Balthazar every time the doctor passed. Each time his glare was met with a smirk and a saucy wink. As thankful as Crowley was for the doctor’s help, this whole “outbreak to breakout” was getting ridiculous.

Sam Winchester had been hunched over the toilet in his and Crowley’s cell for ten minutes before Garth had rushed in with a bucket and told him that they needed to get to the infirmary ASAP. When he got there he was met with Balthazar’s worried face and he desperately desired to forgo the bucket and aim all his pent up “rage” at the doctor.

“Darling you look awful,” Balthazar mused, nodding his head in thanks at Garth who patted Sam’s back hesitantly. Sam glared at him, which just made a look of glee fill the doctor’s eyes. Sam rolled his eyes and tried to push past him, only to end up having a face to face encounter with the floor. From somewhere above him he heard Balthazar stifle a laugh and Garth not even try. He grumbled as the doctor helped get him back on his feet and once he had regained his balance he turned his attention to the prison guard who was wiping tears of laughter from his eyes.

“Marmaduke, you crazy!” Garth laughed, clapping Sam’s shoulder before he turned around and made his way, still laughing, out of the infirmary.

“I don’t think I’ve ever met anyone quite as… unique… as Mr. Fitzgerald,” Balthazar mused as he led Sam to a room in the back.

Crowley looked up from the book he had convinced the nurse to let him read as Sam walked in.

“Hello Moose,” he smiled, receiving a grumble in return. Once Sam was resting comfortably, Balthazar looked over at the shorter man who had dived back into his reading.

“And just what are you doing?” he asked, raising one eyebrow and tilting his head slightly.

Crowley looked up disinterested, “it’s called reading, love, I don’t know if you’ve ever tried it but I assure you it’s a worthwhile endeavor.” From his bed Sam huffed a laugh and closed his eyes.

“No shit Sherlock,” Balthazar retorted, “I meant, where the bloody hell did you get that book?”

“For your information dear Watson, I made a deal with a nurse,” Crowley said, returning to the book in his hands.

Balthazar stared at the convict before smiling mischievously; Sam watched amused as Balthazar shot his hand out and snatched the book away from a now very disgruntled Crowley.

“Sorry love, prisoners aren’t allowed books. Although I guess I could read it to you,” Balthazar winked.

“Give it back,” growled Crowley, but Sam noticed how the corners of his mouth betrayed his stoic command by creeping upwards slightly.

“No,” Balthazar said haughtily, “I shan’t. Now let’s just see what it is that you sold your soul to read.” He flipped the book over and examined the cover, looking back at Crowley in surprise, “Crossroads by Stephen King? I have this book in my office!”

It was Crowley’s turn to smirk, “actually Darling, this book no longer resides in your office as it is currently in this very room.”

Balthazar’s eyes widened slightly and he flipped to the first page, “what the fuck? You had a nurse go into my office to retrieve one of my books for you to read?” He looked up to find Crowley sitting in his bed, arms crossed smugly and a look to match spread across his face. Balthazar seemed to recover quickly however because he closed the distance between himself and the convict, leaning far into Crowley’s personal space, faces only a few inches away.

“You know love,” he murmured, “all you had to do was ask, how could I ever deny you anything?”

Crowley responded beautifully by starting in shock after the doctor who had set the book on Crowley’s lap and was now walking out the door. Beside Crowley, Sam started laughing. Crowley glared at the Winchester, but there was no real heat behind the look, his attentions still mainly focused on what had just happened.

“Looks like someone’s got it bad for the doctor, Crowley I didn’t know you swung that way!”

“Can it Moose.”

\----

Dick Roman was on the verge of a mental breakdown. Somehow a sickness had broken out in his prison, even though no new prisoners had been admitted in a few weeks and since his first day as warden, each employee had to go through a health screening every morning before they were allowed in. It made absolutely no sense, the amount of caution he took to ensure that his prison was in top shape was unparalleled.

“EDGAR,” he shouted to the man sitting patiently outside his office.

“Yes Mr. Roman?”

“I need a list of all the patients affected in the outbreak. Next to their names I want you to put their symptoms, vomiting, fever, shakes, even if their bowel movements have increased. We need to find out what the hell is going on in Folsom.”

Edgar nodded and walked out, shutting the door carefully behind him. Dick moved back to his desk and picked up his phone, dialing a number and sitting down in his chair.

“It’s Roman, I have an assignment for you.”

\----------------

Sam was woken rudely from his slumber by a weary looking Balthazar. Crowley’s condition had worsened and he had been “sent to the hospital” a few hours ago, now it was Sam’s turn. He ruefully accepted the glass of water he knew was laced with some sort of something that would make him sick and mentally prepared himself for what was to come. Five minutes later all hell broke loose. Sam heaved and wretched into the too small bucket placed by his bed, his entire body shaking as he broke out in a sweat, temperature skyrocketing,

“NURSE MASTERS!” he heard Balthazar shout, “WE’VE GOT ANOTHER ONE FOR THE HOSPITAL!”

Meg ran over to the phone and quickly punched in Inias’ number, “Inias, it’s Meg. We have another one for the hospital.”

“We’ll be there in ten,” the voice on the other end of the phone said, a click marking the end of the call. Meg ran into the room where Balthazar appeared to be giving Sam a shot of medicine, Meg however knew that the shot would take effect within the next 10 minutes and cause the younger Winchester to start convulsing followed by the loss of consciousness. This had already been done to seven prisoners, including Fergus Crowley and Dean Winchester. The other five had been given an untraceable poison injected in them as well; killing them shortly after they arrived at the hospital.

When the ambulance arrived the shot had already started to take effect. Sam was already losing consciousness and his body had begun to convulse. Dick Roman watched the proceedings alongside Balthazar, glaring at the prisoner being loaded into the back of the ambulance.

“That makes eight prisoners…” Balthazar sighed, shaking his head forlornly.

“Any idea what’s infecting them?” Dick asked, glancing curiously at the doctor who frowned.

“None at all… I called the hospital earlier but according to them they’ve never seen anything like this before.”

Dick studied the doctor’s face carefully, trying to detect a lie. “Hmm, well try and figure out some sort of cure, even though most of the prisoner’s here are on death row, they should only die from lethal injection, as their punishment states.”

Balthazar chuckled in agreement and turned to the warden. “I’ll go review my notes and make some calls. Maybe some of my friends from school have come across this before.” With that he walked back into the prison.

Dick Roman stood on the pavement, watching the doctor walk through the doors. He retrieved his cell phone and dialed 676.382.8766.

“It’s me; I need everything you can find on Balthazar Roche.”

\----

Sam woke to a pain in his side and a kink in his neck.

“Morning Baby Winchester, the name’s Inias,” the paramedic smiled annoyingly down at Sam who grumbled and sat up carefully.

“What happened?” Sam asked, rubbing his temple and shooting bitchface number three at the man sitting next to him.

“Freedom, freedom happened. We’ve got about an hour and a half until we arrive at the destination so I guess now’s a good time to fill you in on a few things. First, your brother is there along with Castiel Novak, the prison's former warden. Castiel officially resigned a few days after his accident, before he was even made aware of the breakout. Turned out to be a good thing of course, made it easy to get him away from the hospital and to the safe house without raising suspicion. I talked to Bobby Singer a few minutes ago and-”

“Wait, Bobby Singer?”

“Yes, Dean said he’s an old friend of your father's. Just so happens he helped dear Balthazar get into medical school and so naturally he was Dr. Roche’s first choice. Anyway, Bobby said Dean and Castiel are doing well and that Crowley is still recovering but he seems to be okay. Oh, that reminds me,” Inias pulled a book out from the bag next to him, “Balthazar told me to ask you to give this to Crowley for him.” He handed Sam the Crossroads book Crowley had been reading early that morning.

Sam smiled and took the book and the two men spent the rest of the ride in comfortable silence, Inais tapping away on his phone and Sam reading. When they arrived at Singer’s Salvage Dean ran out to meet the ambulance, pulling his brother into a crushing hug.

“Heya Sammy,” he beamed, still hugging the taller man.

“It’s Sam, jerk,” Sam smiled back.

“Bitch.”

Bobby pulled Sam out of Dean’s grasp and pulled him into a hug of his own, greeting the younger Winchester in a similar fashion to how he greeted Dean the day before. When Sam pulled away he smiled at Castiel, who had taken his place next to Dean, their arms wrapped decidedly around each other’s waists. Castiel smiled back and greeted him with, “Hello Sam.”

The group made their way inside and Sam walked over to where Crowley was sitting at the kitchen table.

“Balthazar wanted me to give this to you,” he said, holding out the book. Crowley blushed and smiled softly down at the book.

“Cheeky bastard,” he mused after opening it to the front page. Sam peered over Crowley’s shoulder and saw a little note, written neatly below the title.

**_I could never deny you anything, and it does seem a shame you didn't get to finish._ **

**_It’s a rather good read, very worthwhile._ **

**_I’m greatly looking forward to hearing your thoughts about it._ **

**_XOXO Balthazar._ **

Underneath the note was a phone number and Sam smirked, elbowing the escaped con-man singing “Crowley’s got a boyfriend!” Crowley just sat in his chair smiling down at the note.

Neither noticed when the golden eyed man slipped into the kitchen until Dean, who was leaning on the counter holding a smiling Castiel close, cleared his throat and looked pointedly behind Sam.

The younger Winchester turned around and his smile fell. Gabriel looked very nervous, and very alive. The room was deafeningly silent; the atmosphere tense, it felt as if the whole world was holding its breath.

"Hey there Sammy," Gabriel said sheepishly, caution and concern etched onto the usually chipper face, his voice barely a whisper, rang loudly throughout the room and echoed in the younger Winchester’s ears. Sam’s brown eyes locked with Gabriel’s nervous golden ones, he could hear the beating of his own heart, pounding loud and erratic like his fathers drunken stomps down old wooden stairs. Slowly, he moved over to the once dead man and before his brain registered what his body was doing, he heard a loud *CRACK* as his fist collided with the con-artists face.


	19. Chapter 19

**Summary for the Chapter:**

> In which we have a BM scene. (The Bowel Movement scene? NoooOOOoo! The Boy Mellow-drama scene!)

**Notes for the Chapter:**

> HOLY HIATUS BATMAN!!! I think this was the longest one yet!! Super apologies, 17 days with no word... I am so sorry. Chapter 20 was being a bitch and I lost it like three times (computer crash because my laptop is a fuckwad). Anywaaayyy, I love you all. Let me know what you are thinking of the story so far!! I love to hear what you all have to say! SO COMMENT AND KUDOS!!! <3
> 
> Once again, thank you so much to my wonderful beta Meg who is beyond amazing and whom I love so much I literally can't even. No, seriously, if there was a scale from 1 to Even, I can't. I can't even.

“WHAT THE HECK!” he yelled, whipping around and shooting daggers at his older brother, whose jaw had dropped to the floor. Crowley jumped up and planted himself in between Sam and Gabriel, who was sitting dejectedly on the floor, rubbing his jaw, his golden eyes filled with sadness and regret.

Sam took a moment to recover, staring bewildered at Gabriel, “how are you alive?” he whispered, his body trembling with rage and his eyes filled with betrayal.

“Balthazar…”

Suddenly, manic laughter came pouring from Sam’s mouth. “OH, OF COURSE! Why the hell didn’t I think of that before?!? Naturally, when you watch someone get stabbed and die in front of you, your first thought should be, ‘oh hey, they’re not really dead, just faking it. Maybe the prison doctor had something to do with it’.”

“Sam…” Gabriel started.

“No, you know what, I watched Lucifer stab you. You- you were dead. I mourned over you, I’ve cried myself to sleep every night since your death. And now I find out that you’ve been fine this whole time?"

“Sam…”

“Gabriel Speight, I don’t even want to look at you right now.” With that Sam turned away and stormed up the stairs, walking into his room and throwing himself on the bed. It only took a few seconds before the tears started falling. He buried his face into the pillow and let go of all his self-restraint.

After only a few minutes he heard a light knocking at his door.

“Sammy?” Dean’s slightly muffled voice called out, “hey man, let me in.”

With a groan Sam dragged himself from the bed long enough to unlock the door before he shuffled back and flopped down onto the mattress. He felt it dip beside him when Dean sat down and he soon felt hot tears betray him. Dean stroked Sam’s hair as the younger Winchester wept.

So this was the straw that broke the moose’s back. He felt betrayed and confused, the feeling of helplessness banged around inside his head and it felt as if the devil himself had decided to make a home in his brain.

He barely registered Dean’s words until the question was finished.

“What’d you say?” Sam asked, turning around with tearful eyes and looking up at his older brother.

“I asked if you wanted to go get a burger,” he replied, smiling gently down at Sam, “we’re far enough from Folsom that it should be fine, plus Bobby’s old woman owns a restaurant a few miles out and according to Bobby, she makes a mean cherry pie.”

Sam laughed and nodded, earning a “whoop” and a fist pump from his brother.

They ran downstairs and through the living room only to be met by five pairs of curious eyes.

“We’re going out,” Dean stated, snatching the keys to an old pick-up truck and rummaging through Bobby’s wallet to find a credit card.

“Hold up there ya idjit, just where do you think you’re goin’?” Bobby asked, moving to stand in between Dean and the door.

“We’re gunna go to The Roadhouse, grab some grub, finally meet your old lady, maybe hustle some sorry losers in pool. But most importantly, eat some pie. Folsom was seriously lacking in pie.” Dean shot a spiteful look at Castiel who simply smirked and shot him a sassy wink, the bastard.

Bobby sighed and walked over to the cabinets, opening a drawer and handing a wallet to Sam and one to Dean, “I had these made up for ya, new ID’s as well as credit cards of your own,” he smiled as he held out a pair of keys to Dean, “and I don’t know why you’d wanna take my old beater truck when your Impala is sitting right outside, good as new.”

Dean positively radiated with glee as he cradled the keys in his hand. Without warning he threw his arms around Bobby’s neck and planted a loud kiss on the older man’s cheek.

“Ugh get off me ya idjit,” Bobby complained, but he was smiling and he clapped Dean on the back before turning to Sam. “I have a car for you too, nothin’ fancy but it runs nicely and I redid the interior last week.” He handed a pair of keys to Sam who mimicked Dean’s response, sans the kiss, opting instead for a hug.

“Thanks Bobby,” he said, pulling away and pocketing the keys and wallet.

“Sam,” Gabriel began.

“Okay well we’ll be back later,” Sam rushed, cutting Gabriel off.

“Moose,” said Crowley, glancing over at Gabriel whose face had fallen and who was staring sadly at his feet.

“See ya later,” Sam called out, shoving Dean roughly out the door.

They walked around to the back of the house and upon reaching the Impala, Dean lovingly ran his hand along the hood.

“Hey there baby, did you miss me?” He kissed the top of the car before opening the door and sliding into the driver’s seat with a contented sigh.

“Do you want me to give you two a minute?” Sam snorted and Dean patted the car soothingly.

“Don’t worry baby, he’s just jealous,” he cooed, eliciting a small groan of amused disgust from his little brother who rolled his eyes.

“Can we please go get something to eat now? I’m starving, Balthazar had me throwing up all morning,” Sam complained, running his fingers through his hair.

“What? Why?” Dean asked, starting the car up and driving around to reach the road.

“Part of the escape plan,” Sam grumbled, “It was gross Dean, he put ipecac in the food so like half the prison was throwing up all morning.” He shivered at the memory.

The rest of the ten minute drive was spent in comfortable silence, AC/DC ‘s Back In Black leaking quietly from the speakers. When they arrived at The Roadhouse both men took a moment to gaze at the exterior. Placed out in the middle of nowhere, it looked rundown and abandoned. The brothers stopped just outside the door, sharing a look before Dean brazenly turned the knob and they entered the old building.

The inside was far more appealing than the out, furnished with comfy looking chairs and booths. The back end was raised by three steps and contained a beautiful, well loved, mahogany pool table. There was a small bar near the front, large enough for about three bartenders to comfortably occupy at a time and surrounded by over a dozen mismatched stools. In one of the front corners stood an old rifle game and on the wall to its left hung a dart board. The place smelled faintly of cigarettes and whiskey, both scents overridden by the glorious smell of the patties sizzling away on the grill. Dean absentmindedly licked his lips as he made his way over to the bar, leaving Sam no choice but to follow.

A very familiar looking woman in her late forties with honey gold hair and sharp eyes came out from a room in the back and looked the two men up and down, glaring slightly.

“Sam and Dean Winchester?” She asked, her gaze making the brothers shift in their seats.

“Uhm, yes ma’am…” Dean replied, glancing worriedly at Sam who shrugged and wore a similar worried expression.

“Wrong! When someone asks you if you’re Sam and Dean Winchester, you say no. Don’t you boys know anything about how to be an escapee?” The woman glared at them before reaching under the bar with a sigh and pulling out three glasses and filling each of them up with a few fingers full of an amber liquid. “You two are Harry Spengler and Ed Zeddmore, you’re paranormal experts and basically full out wacka-doos.” She tipped her drink all the way back and finished it in one gulp. Sam and Dean stared at her wide eyed.

She studied the men’s nervous faces curiously, “You’re tryin to figure out where you know me from.”

“You just look very familiar,” Sam explained, Dean nodded silently in agreement.

“I filled in for Castiel before Dick Roman arrived to run the circus, Chief of Police Ellen Harvelle.”

Both men went pale, each trying desperately to figure out a way to escape before they were sent back. Ellen laughed and gave them both a warm smile.

“Listen here you two,” she said, eyes warm, “I’m not gunna turn you in. What you did was very wrong, not the escaping part, although I guess since that wasn’t legal…” she poured each of them another round, “I trust Bobby Singer’s judgment, and if he says that you boys are good then I believe it. From what I heard about what happened to you two in Folsom, well, let’s just say at least you’re out.”

She turned back to the grill and flipped the patty’s sizzling away, “Bobby rang a while ago and told me you two were on your way over. Said you’d be lookin for some burgers. They’ll be ready in about five minutes, until then feel free to drink or just chat. If you want something just holler,” with that she turned around and walked back into the room she had come from earlier.

The brothers sat there in shock, neither one daring to breathe, eyes fixed nervously on the door Ellen had just disappeared behind. When nothing happened they allowed themselves some peace of mind.

“So Sammy,” Dean began, absentmindedly running his finger along the rim of his drink. “We’re free…”

“For now, who knows how long we’ll be able to keep this up. I mean, we’ve had our pictures in the media for years… even if the prison buys it, what if we run into a family member of one of our victims. There’s no way they won’t recognize us. You can’t forget something like that.” Sam took a small sip of his drink and stared at his hands.

“Well, I guess that means it’s time to cut your hair Samantha, maybe with shorter locks you’ll be less recognizable,” Dean smirked, giving Sam’s hair a playful tug only to be swatted away by a giant hand.

“Jerk,” Sam mumbled.

“Bitch.”

Sam looked up and gave Dean a small smile. “Hey Dean, what happened with you and Dick Roman?”

It was Dean’s turn to look at his hands now, his smile quickly sliding off his face. Just then Ellen walked back in with two plates, each containing a bun and a large pile of fries. She walked over to the grill and set the burgers on the buns, delivering the food to the two brothers. Before she walked out she brought the whiskey bottle from the rack and placed it in between them.

“I will come out here to check on this bottle and so help me, if you think I’m going to let you drink and drive then you’re stupider than people think.” Then she was gone again.

The burgers tasted like heaven, especially in comparison to the prison food they had been subjected to.

“Mhhmmmm,” Dean moaned, taking another satisfying bite.

“Dude, can you not?”

Dean grinned mischievously around his burger, “What can I say? I really just love meat.”

Sam groaned and looked down disgustedly at the burger in his hands, “Thanks a lot jerk,” he muttered, setting down the burger and picking instead at the fries, making sure to shoot Dean bitchface number thirteen.

“So… Dick Roman,” Sam started again.

“Dick Roman has this thing about Mafia Bosses. He found out that I was one and he decided that he was going to do his best to break me. I guess he figured out pretty quickly that Folsom runs on a rape scale for how powerful you are. The more powerful the person you make your bitch, the more powerful you are. When Lucifer died and people thought I successfully raped Cas, I became the most powerful man in that hell hole. Obviously Dick couldn’t let that continue. So he decided to make me his bitch…” Dean took another bite of his burger, recalling the tale as if it meant nothing to him. Sam frowned, noticing Dean’s tells. The way his eyes looked anywhere but at Sam, how his whole body went still, the corners of his mouth turned down by a hair.

“We’re safe now,” Sam said, knowing that even though Dean would never admit it, he needed to hear those three words. “What’s in the past is in the past, and even though it might still hurt, we got away. Neither of us will ever see Dick Roman, or Lucifer or Alastair or Azazel or Cain or any of those fugly sons of bitches ever again.”

Dean smiled at his baby brother, “thanks Sammy.”

Sam smiled back and took a bite of his burger, savoring the taste.

“So what about you and Gabriel,” Dean asked, chomping down mercilessly on an unsuspecting fry.

“What about me and Gabriel?”

“You were kinda rude to him…”

“Dean, he died. He let me believe that he died when really he’s just been hiding out at Bobby’s! The day I lost him was literally the day I lost everything! You, him, Lucifer, and before you say what I know you’re going to, yes I do miss Lucifer at times. Sure he wasn’t the nicest of people but there was something there, that is undeniable. I chose Lucifer over Gabe, I enjoyed my time with him for a long time and when he died, I was sad. I was free and that made me happy, but he was gone and as crazy as it seems, I mourned for his death. Maybe not as much as I mourned for Gabe’s, but enough to make Crowley question my sanity. There were times when I would see him lounging around in the cell with me. Once I even thought I heard him singing Stairway to Heaven.” Sam poured himself another drink and consumed it in one swift gulp. “Sure, maybe I didn’t handle the Gabriel situation very well, but how would you feel if you had to watch someone you loved die right in front of you, only to miraculously turn up, very much alive, acting as if nothing happened.”

Dean nodded sadly, “Sammy, I don’t think it was ever Gabriel’s intention to hurt you. I had a conversation with him this morning and from what he said, the idea was completely Balthazar’s. Apparently Balthazar declared him dead and staged the same escape tactic he did with us, delivering a different corpse to the morgue. Inias stayed at Bobby’s until he was sure that Gabriel would be okay, and since then all Gabriel has done is help Bobby around the shop and worry about whether or not you’re going to hate him for being alive.”

Sam sighed, “Dean, I really am happy that Gabriel is alive… I just feel, I don’t know. I’m not mad at him, I just wish we could start over, ya know?”

“Yeah,” Dean nodded, “I know what you mean.” Neither of them noticed the redhead and the blonde that had snuck in and sat down at one of the tables in the corner.

Dean took another bite of his burger and a swig of his whiskey, “After that thing happened with Cas, all I wanted to do was be able to start over. We got that. Sam it’s possible. All the crap Cas and I went through, we survived and now we’re better than ever. I’m sure you and Gabriel are going to be fine, you just need to give him a chance to explain himself. You owe him at least that, you did punch the poor bastard.”

Sam rolled his eyes, “yeah I guess you’re right. So you and Castiel are good now?”

“We’re amazing,” Dean blushed, “Cas is… he’s honestly the best thing that’s ever happened to me. He saw the good in me when no one else did and he believed in me, even when I really didn’t deserve it. Sammy, with our past, I really didn’t think that the Apple Pie life would be possible for us, but it looks like we might actually have a chance. Think about it, me and Cas, you and Gabe-”

“Crowley and Balthazar,” Sam smirked.

Dean’s jaw dropped, “wait what?”

“You should have seen them Dean,” Sam laughed, “I swear, if flirting were an Olympic sport, they would both have a gold medal.”

“I thought you said that Crowley has a wife…”

“He HAD a wife, past tense. Gabriel’s sister, but she died a while back…” Sam explained, still smirking.

“That kinky son of a bitch, I didn’t know he swung that way!”

“Oh God, please don’t tell me you’re going to make a move on him!”

Dean shot an incredulous look at his brother, “How stupid are you man, why would I trade in my blue eyed, bed headed, insanely handsome, and amazingly wonderful in the bedroom, Castiel Novak for Fergus Crowley?”

The women at the table snickered, bringing them to the Winchester’s attention.

“Something funny,” Sam questioned, studying them both.

“Yeah actually,” the redhead replied not missing a beat, “We just never thought we’d be hearing about dear Cassie’s bedroom shenanigans from a total stranger.”

The blonde laughed lightly as she addressed Dean, “do tell, is Cassie a top or a bottom?”

“Is he really loud?” asked the redhead.

The blonde smirked, “Does he like to whisper dirty things?”

The redhead grinned at her companion, “I bet Cassie would love being tied up.”

“That’s enough,” Dean growled, glaring at the two women who collapsed into a fit of giggles.

The redhead looked back at Dean, tears in her eyes. “You must be Dean, I’m Charlie, and this is Jo. We’re good friends of Castiel’s.”

Dean eyed the women suspiciously, “you two are friends of Cas?”

“No stupid,” the blonde, Jo, rolled her eyes, “we just like to sit in bars and listen in on stranger’s conversations and then pretend that we’re friends with whomever they’re talking about.” Charlie snorted into her drink.

Jo walked over and plopped down on the stool next to Dean while Charlie planted herself on the stool next to Sam. “Truth is Dean-o,” Jo said, her eyes narrowing, “we’re not really you’re biggest fans.”

Dean glared back at the blonde, “truth is blondie,” he sneered, “I don’t give a damn about what you two think. And for the record, Cas and I sorted everything out. He understands why I did what I did and he’s forgiven me.”

Charlie frowned, “oh you mean with the car accident and the events that led up to it, no we’re not mad about that anymore. Cassie explained everything to us and made us promise not to hold that against you.”

“Okay,” Dean’s brow furrowed, “then why are you two chicks mad at me?”

“Because you made us miss our Star Wars Marathon!” Jo scoffed, dramatically mimicking being stabbed in the heart.

“You’re serious?” Sam asked, amusement twinkling in his eyes.

“We never joke about Star Wars,” nodded Charlie, smiling, “unless of course we’re making fun of it.”

“Luke,” Jo growled in an excessively low voice as she reached one hand out to Charlie, “I am… your… father.”

Charlie threw herself off the chair, “NOOOOOOOOOOOOO!” she screamed, horrified.

Ellen came bursting from the back, “What the hell is going on up here?”

Charlie shot up from the floor and all the blood drained from Jo’s face.

“Nothing mom, we’re just messin' around,” Jo explained, shooting a glare at Sam and Dean who wore matching smug faces.

Ellen rolled her eyes and heaved a sigh. She walked over to the oven and pulled out a steaming pie, the smell of cherry sweetness filled the air and made Dean dizzy with want. She shot him a look before retreating back into the back room.

“Hey,” Charlie said, suddenly more serious, “I’m glad you and Cassie worked things out, he really likes you, and it seems you really like him to. He needs that. He needs someone who really truly cares for him.”

“Other than Charlie and myself, Cassie doesn’t have friends, or lovers. He had one, Meg, but she was a demon bitch, I’m sure you met her,” Jo continued, eyeing Sam, “she works in the infirmary at Folsom.”

“Seriously, she was the spawn of hell incarnate,” Charlie said and Sam nodded in agreement.

“Sammy had one of those, what was her name?”

“Ruby…” Sam muttered, shame written clearly across his features, “I only dated her because Dad was getting suspicious of my relationship with Chuck.”

“I blame Becky for that one, she couldn’t keep her trap shut,” Dean snarled, “you know she had a thing for you.”

“Yeah I know, but she was crazy…”

“And Ruby wasn’t?”

Jo coughed pointedly, “okay ladies, are you finished?”

Dean rolled his eyes and stuffed what was left of his burger into his mouth.

“So,” Charlie started, grabbing Dean’s beer and taking a swig, “what brings you to our neck of the woods?”

Dean glared at her and snatched the drink back, “Sammy just needed some time to process a few things.”

Jo and Charlie looked at each other for a moment before Jo turned back to face the boys, “Dinner’s on the House then.  But I do have a favor to ask you… Can we come back to Bobby’s with you to see Cas? Mom forbade us to visit without permission, she said you guys would need some time together, but not seeing him has been killing us.”

Dean glanced over at Sam who nodded, “That’s fine with us.”

“IF,” Dean added, “I can have a slice of that pie.”

Charlie beamed and scampered over to the cherry pie Ellen had pulled from the oven, “you can have the whole thing!”


	20. Chapter 20

**Summary for the Chapter:**

> In which Balthazar is told to take a vacation and "Sabriel" has some shit to work out.

Dick Roman sat at his desk, slender fingers entwined, a shit eating smile smeared across his face. Sitting across from him, legs crossed and arms folded sat Balthazar, his smile mirroring Roman’s.

“Balthazar,” Roman began.

“Dick.”

“Hmh,” Dick chuckled, his eyes narrowing slightly and his smile becoming more poisonous. “How are you handling the aftermath of yesterday’s outbreak?”

Balthazar rolled his eyes, “well dear, the whole prison has been sanitized, we lost ten of our prisoners, five more are still in the ICU and we are no closer to finding the cause of the sudden illness.”

Roman was silent for a few moments before nodding curtly at Edgar, who was standing dutifully at the door. Edgar nodded back before leaving the room.

“Balthazar, in light of the recent occurrence, I am bringing in an old friend of mine to watch over things for a while. I would like you to take some time to recover, recoup. Take a month or two, go somewhere sunny and relax.”

Balthazar sat up straighter and was frowning slightly, “And why do you think that I need a break? I can assure you that I am in perfect health. There is no need for me to leave Folsom.”

“I know that’s what you believe,” Roman said sweetly, “but it’s my job to ensure not only the safety of my employees, but also their sanity. I’m afraid I must insist you take some time off.” The door to the office opened and Edgar reappeared, behind him stood a tall man with a slender face, complete with beard and an earring; he waltzed in and shot a smug look at Balthazar who glared back.

“Balthazar,” Roman said, standing up and walking over to the newest member of the meeting, “this is Chet, he will be taking over while you are gone. Take today to show him the ropes, your holiday starts as soon as you’re done. Just go over the basics, let Meg fill him in on the rest.”

Balthazar growled quietly as he stood up and strode out the door, not waiting for Chet. When they reached the infirmary, he rounded on Chet.

“Listen, I don’t know what Dick’s playing at but here are the basic rules. Let Meg handle things until I return. I don’t know you, I don’t know your credentials and I don’t like the idea of a stranger running my infirmary. Meg knows the prisoners and she knows how I run things. If I hear anything bad when I return, or if I find out that you fired any of my staff, I will make sure you are never hired anywhere else. Do you understand?”

Chet smiled back, seemingly unfazed by the threats as he pulled string cheese out of his pocket, unwrapping it and tearing off a string and dangling it in front of the seething doctor.

Balthazar rolled his eyes and let out a huff of annoyance before walking into his office. Chet followed silently and stood in the doorway, munching on his cheese as he watched Balthazar pack up his things.

Three hours and one migraine later, Balthazar sat in a local coffee shop called Kitsune Pond, the owner Amy greeted him with a smile and a wave before returning her attention to her son Jacob. Balthazar smiled back and walked to the counter where a short man with curly hair was waiting, an impish grin on his face.

“What can I get for you today Mr. Roche?” he asked, his squeaky voice grating on the doctors already short nerves.

“Just a Caramel latte, thank you Marv,” he replied, handing over the his credit card when the barista rattled off the amount. He accepted the drink and nodded at the man before making his way over to Amy.

“Oh,” she smiled, looking up as he approached, “Hello Balthazar, how are you today?”

The doctor smiled distractedly, “I’m alright, my boss just sent me on a vacation, I’ve no idea when I’ll be allowed back. Now some idiot is in charge of my infirmary…” he rubbed his temples and let out a forlorn sigh.

Amy smirked, “You’re seriously complaining about taking time off? Taking time away from that hell hole? Balthy, you’ve done nothing but complain about how much you hate that new warden; maybe it’s for the best that you take some time off until Castiel is reinstated. Go somewhere nice, meet someone who sparks your interest and spend this time you have getting to know them. Who knows, maybe you won’t want to come back.”

Balthazar looked over at Jacob who was smashing a purple crayon onto the piece of paper in front of him, perfectly content with the mess of colors that made Unicorn Puke colorless by comparison. He ruffled the kids hair and turned back to Amy, “Thanks Ams,” he said, taking a swig from his cup and pulling his keys from his pocket. “I think I know where I’m going to go.” They exchanged goodbyes and Balthazar made his way back to his car, not paying any attention to the car that pulled out behind him and began following him on the road to nowhere.

 

\---

 

Right after Sam and Dean left, all eyes turned to Gabriel. Crowley got out of his seat and walked over to his friend, laying a hand on his shoulder.

“Listen here darling, Moose will come around eventually. I’m sure he just needs some time to adjust. Spending some quality time with Squirrel will do him well.”

Gabe continued to stare at the floor. His shoulders were slumped and he was shaking slightly. Castiel walked into the living room and returned a moment later with a blanket which he draped around the escapee. Gabriel’s questioning golden eyes shot up to meet Castiel’s calm cerulean blue ones, Castiel gave him a small smile and sat down on the floor next to him.

“Gabriel, the Winchesters are… interesting men. If Sam is anything like Dean, he’ll come around.”

Gabriel frowned at the warden, “and why should I trust you? How do I know that you’re not just going to turn us all in? Don’t tell me that I can trust you because you and Dean share some sort of profound bond, because that ain’t gunna fly.”

Castiel looked away sadly, “I know, I’m just the warden who lost his mind and fell for the convict. As unlikely as that sounds, that’s what happened. I don’t know when, I don’t know how, all I know is that before I met Dean I would wake up not wanting to go to work, but then I met him and the idea of seeing him again would get me excited about spending all day doing boring paperwork. Because at least I would be able to talk to him for a little while. I know it sounds sappy, Dean would call this a ‘Chick-flick moment’ but it’s also the truth. I know Sam loves you, from the way he didn’t talk about you after your death, it was obvious. He spiraled downwards; he blamed himself for your death. The amount of times I was called to his cell because he refused to eat was astonishing. Now here you are, alive, no warning. Can you blame him for being upset? He just started to finish mourning you and now you’re back. It’s a wonder he didn’t do more than just punch you.”

Gabriel continued to glare at Castiel, but his face had softened. “I just-” he started, looking away, “I never wanted to hurt him, everything I did was to protect him and I guess it didn’t cross my mind that he would be upset.”

“What did you think was going to happen?” Castiel snorted, “that he was going to run into your arms and carry you up to the bedroom and you two were going to spend the next week getting ‘reacquainted’?”

Gabriel didn’t answer and Castiel’s smile fell. “Gabriel, give him some time. He’ll come around, Dean’s talking to him and I know that if anyone can knock some sense into the head of a Winchester, it’s another Winchester.”

“What’s going on with you and Dean?” Gabriel asked, watching Castiel carefully.

Cas blushed and looked down at his hands, “Dean and I have been through a bit, not the same as you and Sam, but we’ve suffered our share of hardships. The night that I left, Dean had tried to rape me. I later found out that he had only done so because Lucifer had ordered that if he didn’t, both he and Sam were to be killed. Needless to say, when I left Folsom that night I wasn’t exactly fit to be driving and I ended up getting into a really bad accident, broken bones, trip to the ER, the whole shebang. I was able to keep some tabs on Dean through Balthazar, and, well, I’m sure you’ve heard some of what happened through Bobby and Rufus.”

Gabriel smirked, “I also heard some of what happened the other night through the walls. You should keep in mind next time that just because you have a record playing in the background, we can still hear you.”

Castiel’s eyes widened in horror and uncomfortable blush spread across his face. “I- we- you- but-” he spluttered, he looked over to Bobby for some sort of help but all the old man did was give him this He ain’t lyin’ that’s for damn sure look before turning to cast a scowl at Gabriel.

“What Dean and Castiel get up to in the bedroom isn’t any concern of ours,” he paused to take a swig of his beer before continuing, looking at Castiel out of the corner of his eye, “no matter how loud they get.”

Castiel was going to die. This was it for him, everything that he’d gone through since the Winchesters came to Folsom and he was going to die from embarrassment. Gabriel looked as if he was going to protest but stopped abruptly when the lock on the door clicked.

Castiel felt his jaw drop when he saw Dean walking in with Charlie’s arm latched securely around his waist. They were both laughing about something and talking as if they’d known each other for years. Jo and Sam meandered in after them, quietly discussing their own topic, not paying any attention to the two loudmouths. Out of the corner of his eye, Cas noticed Gabe quietly slip out of the room before Sam had the chance to approach (or ignore) him, Crowley let out a sad sigh and followed. When Dean spotted Castiel he crossed quickly over to him and gently cupped the warden’s face.

“Hey Angel,” he mumbled as he pressed their lips together softly, “missed you.”

Castiel felt his blush returning, “I missed you too Dean,” he sighed, leaning into the kiss and wrapping his arms around Dean’s waist. Dean hummed contentedly as he drew him closer still, Castiel was vaguely aware that the rest of the room had gone exceedingly quiet and after planting a chaste kiss on Dean’s lips he pulled away and looked around the room. Sam was staring at the floor, a light blush covering his cheeks, refusing to meet Castiel’s gaze. Bobby fondly muttered, “Idjits” under his breath before snatching up two beers offering one to Sam, who accepted it gratefully, as they left the kitchen.  Jo and Charlie stood smugly, their all too knowing looks made Castiel squirm a little, causing Dean to turn his attention to the two women. He rolled his eyes and pulled Castiel back to him, still watching Charlie and Jo.

“Ya know,” he said with a wink, “If you really want a show I can probably come up with something.” On the word ‘up’ he palmed the globes of Castiel’s ass, making their groins press together slightly and eliciting an unexpected moan from Castiel, who’s ears went red immediately as he halfheartedly tried to paw his way out of Dean’s grasp.

“Don’t stop on our account Dean-o,” Charlie winked back, “God only knows that Cassie is in need of some serious action! I’m tempted to make you bend him over the table and give it to him right now, just to make sure he’s actually getting some action.”

Jo rolled her eyes and punched Charlie soft enough as to not hurt, but hard enough as to get her point across. Castiel’s breath hitched when he felt Dean start to get hard and he unconsciously licked his lips at the thought, drawing a coy smile to Dean’s lips.

“Sorry Charmander,” Dean shot back at the redhead, “but I think you’ll have to be good with just hearing for now. If you’ll excuse us, I have a rather hard and lengthy topic I need to discuss with Cas in private.”

Charlie crinkled up her nose in mock disgust, “‘hard and lengthy’? Really Winchester, can you be any more obvious?”

“Don’t…” Castiel warned, but it was too late.

“I’m going to take ‘Cassie’ upstairs and fuck him so hard he won’t be sitting right for at least a week,” Dean grinned taking hold of Cas’ hand and pulling him out of the room and up the stairs.

Cas heard Charlie shout, “TMI!!” from the kitchen, but quickly forgot when he felt Dean start to suck at his collarbone.

 

\---

 

Back downstairs, Sam and Bobby sat on the couch, equally disgusted and happy when Dean and Cas rushed upstairs.

“It’s about time Dean found someone good,” Bobby said, peeling his eyes from the staircase the two men had disappeared up and returning his attention to his beer and to the younger Winchester sitting opposite him.

Sam smiled and nodded, “I must admit, I was worried when I first found out about Dean liking Castiel, I mean Warden/Prisoner relationships usually don’t end well. I feared that Dean only liked Cas because he was one of the few people who was actually nice to Dean.” Sam sighed and took a gulp of his beer, “the truth is Bobby, that place was awful. Dean had it worse than I did, but I think part of that was purposeful. He’s always done his best to protect me and that didn’t stop, even when he was the one who needed protecting more.”

Bobby sighed and waited until Sam returned his gaze before saying gently, “Listen here son, what happened in Folsom Prison, it’s over. It doesn’t matter what you did or didn’t do, Dean doesn’t seem to hold anything against you. What matters now is that you all have clean slates, you can start over again.” Sam shrugged and looked down at his hands. “I’m not telling you what to do,” Bobby sighed, “but I am telling you that there is a certain golden haired man who has not stopped talking about you since the day he arrived. If you have any sort of common sense in that smart ass head of yours, I’m sure it would be telling you to sac up and go talk to him.”

Sam looked up forlornly, “Bobby, he died. I- I mourned his death, I slept in his bed because it smelled like him, hell, the times I woke up in the middle of the night to Crowley trying to comfort me because I’d been calling out for Gabe is- it’s embarrassing. Then I get here, and there he is. And I was happy, until it all came crashing down. All the nights I spent crying myself to sleep, the times Crowley literally had to shove food in my mouth because I didn’t want to eat anything. I was sent to the infirmary so many times because apparently I looked like Death itself. The only person I talked to was Crowley, and even then most of the time we talked he was the one who asked all the questions. I couldn’t be happy that he was alive because it was easier to be angry.” Sam felt a hot tear betray him and run down his cheek; he swiped it away and looked back at his hands, “I still love him, but… I’m afraid that as soon as I let myself go, I’m just going to lose him again.”

 

\--

 

Sitting on the other side of the wall, Gabriel leaned his head back to rest it against the wall as tears streamed down either side of his face. Crowley sat quietly next to him, respectfully looking at the floorboards, not saying anything. Silent sobs shook Gabriel’s body and Crowley was reminded of sitting in the cell with Sam when he cried. If Sam knew what Gabe was going through, maybe he would realize that Gabriel wasjust as in love with him as he was with Gabe… maybe they could start over.

 

\--

 

Bobby rubbed his face in his hands, “Sam, I have a difficult time believing that Gabriel Speight is ever going to let you out of his sights again if you ‘let yourself go’ and tell him that you love him. Just, make sure that you’re being honest with each other. And take some time to get to know each other outside of prison walls before you go confessing your love. The last thing that poor man needs is you telling him you love him, then going back on your word and leaving him.”

Sam looked up, horrified at the idea, “I would nev-”

“I know you wouldn’t do it on purpose, you’re a good kid. But I don’t want that to even be a possibility. You gotta remember, he’s been wanting you back just as much as you’ve been wanting him back- don’t deny it boy, Crowley and I had a nice little chat about some things when you and Dean went out for your talk,” Bobby chucked at the bewildered look on Sam’s face, “don’t worry, he didn’t tell me anything he didn’t think I didn’t need to hear.”

A knock at the door interrupted their conversation; Bobby cursed and turned curiously to Sam, who shrugged. Whoever it was knocked again and with a grunt Bobby heaved himself out of his armchair.

Thinking that Sam had gone with Bobby, Gabriel timidly entered the living room, followed by Crowley. He stopped short when he saw Sam still sitting on the couch, watching him.

“Uhm…” he started, looking pleadingly over at Crowley who raised an eyebrow before turning on his heel and walking into the kitchen, leaving the two men alone.

Sam noticed that a bruise had appeared on Gabriel’s jaw and he winced at the sight, “C’mere,” he said gesturing to the cushion next to him. Gabriel’s eyes wandered to the kitchen and he looked like he was contemplating making a run for it. But then he turned back to Sam and let out a defeated sigh, his shoulders slumped and he carefully made his way over to where Sam was waiting for him.

Gabriel had barely sat down before he was being pulled into the strong arms of Sam Winchester. He let out the breath he didn’t realize he’d been holding and allowed himself to return the hug. He smiled when he felt Sam squeeze tighter and without thinking, he nestled his face into the crook of Sam’s neck.

“I missed you,” Sam sighed, breathing in Gabriel’s scent as he buried his nose into the con-artists golden hair.

“I’m so sorry Samsquatch,” Gabe mumbled, his voice slightly muffled. Sam pulled them apart and looked into Gabriel’s eyes. The pair of golden eyes starting back at him were full of regret and sorrow, but in their depths there was a glimmer of hope. Sam pressed his lips to Gabriel’s forehead and let out a sigh.

"Gabe, just- just promise me that from now on, no more secrets. No more fake deaths, no more- just no more leaving… okay?”

Gabriel sniffed and ran his palms over Sam’s biceps, watching as goose bumps rose on Sam’s skin with each glide, he nodded and looked back up at Sam who was watching him very carefully.

“No more leaving...” he repeated, and Sam smiled before threading his fingers through Gabe’s hair and pulling him into a soft kiss. Gabriel let out a hum of happiness and moved with Sam when he scooted them to be lying down on the couch. Gabriel pulled away and tucked his face back in the crook of Sam’s neck, closing his eyes and smiling when he felt Sam wrap his arms around him. They had forgotten all about the mysterious visitor and when Bobby came back into the living room, he found Sam and Gabriel fast asleep. He smiled to himself and grabbed a blanket from inside the trunk that was used as a coffee table; he spread it over the two men and quietly slipped back into the kitchen where Jo, Charlie, Crowley and Balthazar sat around the table. 


	21. Chapter 21

**Summary for the Chapter:**

> In which Balthazar is sent on 'vacation' and Sam and Gabe get down and dirty.

When Bobby opened the door he was more than a little surprised to see Balthazar standing on his porch, a smile dancing on his lips. He pulled the doctor into a short hug of greeting, slapping him on the back a few times before pulling away and grinning back.

“Good to see ya doctor,” he said, ushering the younger man inside, “though I must say that I am a little shocked.”

Balthazar put his hand to his heart dramatically and whimpered, “you mean I’m not allowed to visit my favorite grandfather whenever I want?”

“I ain’t your grandfather you idjit,” he grumbled, rolling his eyes and strolling past Balthazar, leading the way into the kitchen. Charlie and Jo looked up with curious eyes at the newest arrival to the seemingly ever growing group; Balthazar winked salaciously at Jo, earning a giggle from her and a growl from Charlie, who scooted her chair closer to the blonde and narrowed her eyes at the doctor.

“Don’t worry love,” he said, walking over to the cabinet to grab an old bottle of wine and a glass, “I’m not the sort of man who goes after things that are already taken.” He poured his drink and swirled the dark red liquid, giving it an absentminded sniff before bringing the cup to his lips and taking a slow sip. “Besides,” he continued, “I already have someone I’m going after, and I believe that getting them will require all of my attention.” He winked at Charlie who rolled her eyes, but never the less looked significantly more comfortable.

“So what brings you to my neck of the woods boy?” Bobby asked, sitting down in a chair across from Charlie and Jo and motioning for Balthazar to sit down as well.

The doctor glided over to the table and fell dramatically into his seat, “I’ve been made to go on holiday,” he whined, “can you believe it? Ugh, the audacity that man has! To make someone go on holiday, why, it’s unheard of!” 

Silence surrounded the table while Balthazar glanced from person to person, confused as to why no one was jumping to agree with him, then a rumble of laughter emitted from Bobby, followed by Jo’s airy laughs and Charlie’s warm cackles.

“You’re not seriously pissed because they told you to take a vacation are you?” Charlie laughed, looking at him with a mixture of amusement and disbelief.

Balthazar said nothing for a moment before he too started to laugh at how ridiculous he was being. They sent him on holiday for goodness sake! He had not only started the whole outbreak, but he also assisted in four break outs, and the only thing that happened to him was that he had been sent off to go enjoy some sun. Out of the corner of his eye he saw Crossroads on the table next to Crowley, and when he looked up Crowley grinned at him from behind the cup of steaming tea; Balthazar grinned back and both men jumped slightly when Charlie pointedly cleared her throat.

Balthazar was pleased to see Crowley’s cheeks redden slightly and he smiled to himself at the small triumph.

“Perhaps,” the doctor started, “I could get a tour of the place. It’s been a while since I was here last and I’m not quite sure I remember where everything is.”

“What are you talkin’ about?” Bobby huffed, “You were here la- OW! Joanna Beth Harvell what the hell was that for!?”

“I don’t know what you’re talking about old man. Crowley, why don’t you give the good doctor a tour of the place?”

Crowley rolled his eyes but couldn’t help the smile that pulled on the corners of his mouth. He turned to Balthazar, “What do you say love? I’m more than happy to show around, I must say I’ve found some of the best private nooks and crannies in my attempts to get some peace and quiet.”

“Darling, I would just love for you to show me your private nooks and crannies,” Balthazar winked as he stood up. He walked over to where Crowley was sitting and rested his hands on each of the armrests, leaning down so that his lips brushed against the con-artists ear, “but you’re going to have to forgive me in my attempts to destroy your peace and quiet, I promise I will do my best to make you scream.”

Crowley shivered beneath him and when Balthazar pulled away he found the con-artist smirking up at him, eyebrow raised, “Shall we get started then?”

When they entered the living room Balthazar chucked at the sight of Sam and Gabriel cuddled up on the couch.

"I see you two are finally reunited," he said loudly, startling them both from their sleep.

Sam glowered at the doctor and muttered a curse under his breath, causing Gabriel to do his best to stifle his laughter at the remark. Balthazar's eyes narrowed mischievously and he wrapped an arm around Crowley's waist, drawing him closer. 

"You have no idea how difficult it was for us to keep Gabriel's survival a secret," he continued, sighing dramatically and gazing off into the distance, "but alas we were under strict orders not to inform you."

Sam looked incredulously at the doctor, "We?" he repeated.

"Fergus and I. Believe you me Sammy, we would have told you if we could, but unfortunately we couldn't. It was for your own good though. I mean can you imagine if we had told you the truth?"

Sam's eyes narrowed as realization struck.

"You knew?" He hissed at Crowley, anger seeping through his voice.

"Moose, I'm sorry but we couldn't risk telling you..."

Sam turned suddenly on Gabriel, "You fucking told Crowley but you didn't tell me? Do you know what I went through? Can you even comprehend what it was like for me? That whole time I suffered while everyone else in Folsom fucking knew!"

"Not everyone," Balthazar corrected, "just myself, Fergus and my medical staff. So only maybe 20 or so people in total. Not including Bobby, Rufus, Ellen, Jo and Charlie."

"So seven people I actually know, and twenty strangers? How does that make it any better? I should have known." Sam spat as he pushed himself off the couch and stormed upstairs.

"Sammy!" Gabriel called after him, jumping to his feet and scampering to follow Sam.

"What the bloody hell made you think that was a good idea?" Crowley snarled, pushing Balthazar away and turning an icy glare on him.

"They had issues that obviously needed sorting and Sam was going to find out sooner or later. At least this way they can sort out all their problems before taking anything any further. I did this for their own good." Balthazar explained, meandering over to a bookshelf on the other side of the room.

"Now," he drawled, taking his time to rake his eyes up and down Crowley's figure, "I believe I have some private nooks and crannies to defile."

 

\----

 

Gabriel sat cautiously at the end of the bed, watching Sam pace back and forth in a tired line, the steady thumps of his footsteps strangely soothing.

“Sam,” Gabriel started, his voice low as to not startle the taller man. Sam merely grunted in response, mind elsewhere.

“Sam please talk to me. We can’t fix this unless we’re both open with each other from here on out. I’m sorry that I couldn’t tell you I was still alive, believe me I wanted to but I couldn’t. You have to understand that Sammy. Please I really do think that if we tried we can,” Gabriel faltered slightly when Sam’s eyes pierced his own. He subconsciously licked his lips, he felt the heat rise to his cheeks when he noticed the taller man’s gaze follow the tiny movement.

“Sam?” Gabriel let out in a small squeak as he was shoved back onto the bed. He shrank into the mattress as Sam crawled over him, placing his knees snugly around the con-artists waist and his palms on either side of Gabriel’s head. Gabe laid perfectly still, staring up at the younger man, unable to breath. Sam studied him for a moment, then with a small growl he bent down and closed the gap between them.

Gabriel felt the air rush out of his lungs and the blood flow swiftly south. His eyes closed and his hands came up to cup Sam’s face, drawing him closer. They stayed like that for only a second before Sam pulled away roughly and captured Gabriel’s wrists in his hands. A look of contempt consumed his usually sweet face as he tugged Gabe’s hands above his head. Gabriel struggled half-heartedly but was only met with a dark chuckle from Sam as he moved them so that both of Gabriel’s wrists were trapped in only one of his large hands, while the other hand mockingly caressed Gabriel’s face.

“Did you really think that just because you say you’re sorry, suddenly everything will be alright?” Sam sneered, his hand slowly ghosting over Gabriel’s neck, traveling down. “Do you really think that I’m that easy?” He chuckled again and Gabriel felt an uncomfortable weight in his gut; he whimpered softly when Sam’s hand tightened around his wrists and pulled them further over his head. He felt Sam’s other hand press on the center of his chest and it was in that vulnerable state that his mind chose to remind him that Sam Winchester had been thrown in Folsom for murder.  He shivered at the thought and tried again to squirm out of the Winchester’s grasp.

“Not so fast,” Sam smirked, tightening his grip again and applying more pressure, “I’m not finished yet. You see, when I first found out that you were actually alive, I was happy, but also angry that you hadn’t told me; I wept for you and mourned over your supposed death. But I thought that maybe, just maybe, you would at least have the decency to be honest with me after that. So I gave you another chance. Now here we are, are you’re telling me that we both need to be honest with each other? I’m not the one who faked my own death; I’m not the one who didn’t have the decency to even try to let the other one know that I was okay. I am however the one who has been honest at all times about how I feel, about what I want and about who I really am.” Sam bent down and sucked a dark hickey onto Gabe’s neck. Gabriel winced slightly at the roughness but didn’t try to move away from it.

“You want me to be completely open and honest?” Sam growled, “Fine, you are mine and only mine. I don’t you to ever forget that. I don’t care about our pasts and I don’t want to be mad at you for lying to me for so long, but Gabriel you have to understand that loosing you…” Sam’s voice hitched slightly and the con-artist beneath him let out a small whimper.

“Sammy, if there had been any way to let you know that I was still alive… but Lucifer’s men were still watching you and Dean, they expected you to be in mourning over that great big bag of dicks and I couldn’t run the risk of giving you good news and them getting suspicious. If they knew that I had survived and then escaped you and your brother would still be in that hell hole.” Golden eyes pierced through hazel ones and Sam let out a small sigh.

Then the con-artist’s hands were free and he felt himself being pulled up into the arms of the younger Winchester. Sam could smell a hint of butterscotch as Gabriel nestled his face into the crook of Sam’s neck, and he buried his nose in the mess of soft golden hair, planting a soft kiss where his lips touched. When he inhaled deeply Gabriel snorted a laugh and pulled away, a faint glint of mischief in his eyes.

“Are you seriously smelling me?”

Sam rolled his eyes, “shuddup and come here,” he grumbled, pulling the shorter man close and pressing their lips together in a soft embrace. 

“I’m still mad at you.”

“I would be worried if you weren’t.”

“...I am happy that you’re not dead.”

“So am I Sambo,” Gabriel winked. He studied Sam’s face for a moment before gently pushing Sam to lay back on the bed. Slowly he moved over Sam, hands running up and down Sam’s body.

“Gabe,” Sam whispered, arching his back and reaching around to grab just below Gabriel’s ass. He massaged Gabriel’s upper legs and inched slowly inwards until he was massaging his inner thighs. Gabriel pressed his groin against Sam’s causing their hardening dicks to rub against each other. Sam let out a gasp and squeezed the con-artists thighs harder, causing the shorter man to thrust involuntarily. Sam allowed his hands to wander upwards and when he had a firm hold on Gabriel’s ass, he started pulling them closer together meeting each other’s thrusts in perfect rhythm. Gabriel went to work on marking Sam up; making sure that the rest of the world knew that the insanely sexy man beneath him was his and only his.

Sam writhed beneath Gabriel's attention and soon they were both wriggling out of their clothes and falling back together. The feeling of skin against hot skin nearly drove both men to their breaking point, but wanting to make it last longer they held on. Gabriel was careful not to let their bare erections touch just yet, and he pulled off of Sam just before the taller man could pull him completely down.

When he was sure Sam was watching, Gabriel traveled down Sam’s body, licking and kissing every inch of skin he could. By the time he had reached Sam’s belly button, the younger Winchester’s breath had gone erratic and Gabriel could feel the heat radiating off of Sam’s erection. Drops of cum were already spilling over and Gabriel locked eyes with Sam before flicking out his tongue for a taste. Sam’s hips bucked up and he let out a wonton moan that was loud enough the guards back at Folsom probably heard it. Gabriel smirked and waited until he had Sam’s full attention once more before taking Sam’s dick in his mouth and swallowing it down completely in one swift move, stopping only when his nose was nestled in the surprisingly soft hairs at the base of Sam’s dick. 

Sam shuddered, trying hard not to thrust up and hurt this amazing man who somehow knew exactly what he liked. Sam gently pulled on Gabriel’s hair, raising Goosebumps up the con-artists body. Gabriel swallowed around Sam’s cock, causing Sam to gasp sharply and tighten his grip on Gabriel’s hair. Gabe went to work humming and sucking, making sure to bring Sam to the edge of release before he pulled off with a smack. Sam pulled him up quickly and captured Gabe’s lips in his own, moaning at the taste of himself on the con-artists eager tongue. Suddenly Gabriel let out a soft cry as the fingers he had been working inside himself hit gold. Sam sat there awestruck for only a moment before he flipped their positions so that Gabriel, still working himself open, was spread out on the bed beneath Sam. Gabriel’s eyes fluttered closed as he continued to thrust his fingers in and out, a sultry moan escaping his lips every time he grazed his prostate. Sam watched enraptured as Gabriel became more and more desperate, his hard cock dripping cum into the trail of hair leading from his pelvis to his belly button.

“Sammy,” Gabriel moaned, “I’m ready…. Please. I- oh god!- I- I need you Sammy please!”

Sam quickly lubed himself up and carefully pulled Gabriel’s fingers away from his ass, bending down to kiss away the con-artists moan at the loss as he added more lube around and inside Gabriel’s hole..

“ ‘S okay babe, I’ve got you. I’m gonna make this real good for us.” Sam crawled over the smaller man, grabbing his hips and lifting them slightly, he grabbed a pillow and put it underneath Gabriel before he lined himself up with Gabe’s entrance.

“I’ve got you,” he whispered, pressing soft kisses over every inch of skin he could find as he pushed slowly in. He went slowly, pressing in inch by aggravating inch, making sure to pause every few seconds to allow Gabriel time to get situated.

“Sammy,” Gabe plead as he lifted his legs and wrapped them around Sam’s hips, hooking his feet so that they rested in the divots above each of Sam’s ass cheeks. 

“It’s okay Gabe,” Sam panted, straining to maintain his slow pace. He barely registered the hiss of aggravation Gabriel emitted before Gabriel’s hands took hold of Sam’s upper thighs and pulled him fully in in one quick motion, thrusting his hips up as he pulled Sam’s down. Gabriel let out a yell and arched his back at the feeling of being filled so quickly and Sam had to bite his lip hard and bury his face in Gabriel’s neck in order to keep himself from coming right then.

They lay there shaking and panting, each grasping onto the edge of sanity, trying to stay put together for a little while longer. It was only after a few minutes of clutching onto each other when Gabriel pressed his lips into Sam’s hair.

“Sam… move.” He whined, and so Sam did just that. Starting out on a gentle rhythm, in and out in time with Gabriel’s breathing. He kept his pace, doing his best to draw of the experience for as long as he could, wanting to give Gabriel everything he had.

“Sam- oh- oh god Sammy! So good- ah- so good for me,” Gabriel panted, one hand finding purchase in Sam’s mane while the other grabbed Sam’s neck, pulling the taller man down for a heated embrace. Sam’s hips faltered and his thrusts became more and more erratic as he got closer.

“So tight for me- so hot,” he moaned, savoring the sound of Gabriel coming undone. “I want you to come baby, just like this. Just listening to my voice while I thrust my dick inside you.”

Gabriel moaned and reached down to take hold of his dripping cock, Sam swatted him away and leaned closer so that his lips brushed against Gabriel’s ear.

“Untouched,” he breathed. Gabriel let out a whimper that sent Sam’s head reeling. His thrusts quickened involuntarily and his mouth started talking on it’s own accord.

“Come Gabriel, come for me. You belong to me and only me. I want you to come untouched, I want you to cover our chests with your hot cum. When we’re done I want you to lick it off me, can you do that baby? After I come deep in your ass, will you be a good little cockslut and lick up the mess you’ve made?”

Gabriel came without warning, screaming Sam’s name in praise as hot ropes painted their chests. His hole clenching tight around Sam’s cock, causing the Winchester to cry out as he came fully sheathed deep inside the con-artist. Sam thrust his hips gently, milking out his orgasm while he whispered praises into Gabriel’s ear.

“Wha-?” Sam huffed when Gabriel roughly pushed him off, his confusion quickly turning to awe when Gabriel climbed on top of him, straddling his hips and bending down. He made sure to lock eyes with Sam before he stuck out his tongue and licked up a stripe of semen that shone on Sam’s chest.

“Fuck,” Sam groaned, completely mesmerized as Gabriel slowly licked up every drop of cum, locking eyes with Sam once again when he had finished, licking his lips and letting out a small moan of satisfaction. Gabriel slowly crawled off Sam and worked his way underneath the duvet, his lips curling into a curious smile as he patted the space next to him.

“Care to join me in my post-coital bliss Samsquatch?” He smirked. Sam rolled his eyes and huffed a laugh as he maneuvered his long limbs under the duvet next to Gabe. As soon as his head hit the pillow he felt Gabriel slither around him, his arm resting protectively over Sam’s chest and one of his legs hitched up and snuggled in between Sam’s. Sam smiled and wrapped his arms around Gabriel’s shoulders, drawing him closer.

“G’night Sammy,” Gabriel sighed into Sam’s chest.

“Good night Gabriel,” Sam mumbled into the con-artist’s hair.

“Love you.”

“I love you too.”

 


	22. Chapter 22

**Summary for the Chapter:**

> In which Marv is assigned a keeper, and a special someone from Dean's past throw's Castiel into the arms of the green eyed monster.

The next day Bobby, Jo, and Charlie left early in the morning in order to help Ellen open The Roadhouse, promising to return as soon as they could escape. The remaining three couples had settled themselves in Bobby’s living room and decided to watch some cheesy movie Gabriel had chosen.

“Shawn of the Dead is a classic Sam.”

“I don’t care if it’s a ‘classic’, it’s boring.”

“Keep saying things like that and you’ll find yourself without anyone to suck your dick.”

Dean made a gagging sound from where he sat, a sleeping Castiel curled comfortably around him. 

Balthazar excused himself halfway through the movie, claiming that he needed to “take a piss,” five minutes later Crowley got up and walked out without a word. After a while a faint banging could be heard from upstairs, barely audible beneath the sound of the rain beating heavily on the windows. A crack of thunder from outside caused Castiel to wake with a start. 

“Shh, it’s okay Cas, just thunder,” Dean reassured, running his fingers gently through Castiel’s hair. Cas smiled sleepily at him before returning his head to Dean’s shoulder and drifting off again.

“So,” Gabriel drawled, leaning back against Sam, “tell me Winchesters, how does it feel to be a part of a household made of domestic couples?”

Sam smiled and pulled Gabe closer while Dean just rolled his eyes and turned his attention back to the movie. Gently he readjusted his position so that he was laying on the couch with Cas laying half on top of him, the rest of him pressed safely against the back of the couch. Dean smiled at his sleeping boyfriend before he too closed his eyes.

Gabe convinced Sam that they should marathon all of Simon Pegg’s movies, and it wasn’t until they had finished Hot Fuzz and were halfway through The World’s End that Crowley and Balthazar meandered downstairs and resumed their movie watching positions.

 

\------------------

 

Over at Folsom Marv sat across from Dick, folders stacked neatly in a pile rested in the middle of the desk.

“So, the infamous Winchesters are alive after all.”

“Yes Sir, so are Gabriel Speight and Fergus Crowley.”

“And Balthazar and our sweet Castiel are with them?”

“In more ways then just one,” Marv snickered.

“You’re sure this is all the information that was possible to gather?” Dick questioned, eyebrow raised quizzically.

“I already told you,” Marv huffed, “I found out everything that I could without making myself known. Balthazar was easiest because he’s good friends with my day job boss, and all I had to do for the rest of them was hang around that stupid Roadhouse owned by Ellen Harvelle. Apparently one of her bartenders, Benny, used to be in a.. uhm... ‘relationship’ with Dean. Before Dean turned murderous.”

“And where is this ‘Benny’ currently?”

“As far as I could tell, he’s still a bartender at The Roadhouse. He took the past few weeks off work to visit a cousin of his down south, but he should be returning today or tomorrow.”

Roman smiled and nodded towards Chet, who swooped down and gathered the files, promptly whisking them away. When the door was clicked shut Roman turned his interest to his computer. 

“So far Operation Meta has been going along nicely, but I would like to see a quicker outcome next time. Don’t be so afraid to let them see you, you’re a nobody to them. More likely then not, no one will be paying attention to a little rodent of a man such as yourself,” Dick said, clicking away at his keyboard.

“Nobody?” Marv whined, “With all the knowledge that I have in my ‘rodent like self’ I am practically a God!”

Roman looked back at the indignant man, “You? God? Do you know how foolish you sound? Can you even try to comprehend what that would mean? You’re not God, you’re a hired hand. The only reason you’re so good at discreetly collecting information is because no one takes the time to notice that you exist. You’re not some trusted all knowing confidant. You’re just someone who found a way to be paid for what you do naturally, be invisible. You don’t know what it’s like to be in charge. In fact I’m willing to wager you’ve never shoplifted, let alone decide who is going to live and who is going to die,” Roman chuckled, “Don’t pretend that you are more then worthless. You, my little friend, are as expendable as they come. That’s what makes you perfect for this job.”

Marv sat in silent awe, mouth agape. His breath quivered as he spoke, “I got you all this information. Information you needed in order to keep your precious operation going. I’m the one who found out that the Winchesters and their little gang of fuck-buddies are still alive and healthy. Without me, you wouldn’t have known any of this!”

“NO.” Dick sneered, leaning forward slightly over the desk, hands now folded menacingly in front of him. “Without you, I would have some other lowlife, good for nothing, self centered sap sitting across from me, handing over the same information. Let’s get this one thing cleared up right now Marv, you are easily replaced. Anyone will spy on people for the right price and most other people would be less of a pain in my ass. Until Operation Meta is over, I own you. If you don’t like that, I can arrange for Chet to ‘debrief’ you, if you catch my drift.” 

Marv frowned at the threat but stopped arguing.

Roman leaned back and pressed a button on his phone, “Chet, please bring in the new hire.” He turned back to Marv, his face less intimidating then before, “Marv, I had hoped that you wouldn’t become too much of an issue, but after this little chat I see that I might need to implement some cautionary measures.”

Chet entered the room, a tall man with dirty blonde hair trailing behind him. The man was wearing a black leather jacket over a zip-up-hoodie with a red shirt hugging his trim torso. His eyes were slightly squinted as if he were in a constant state of confusion and his nine-o-clock stubble defined is already sharp jawline perfectly. 

“Marv, this is Gadreel, he will be assisting you from here on out. Make no mistake, his main job is to make sure that you don’t get too out of line, however, he has also been instructed to help you succeed in the mission that I have given you.”

Gadreel nodded slightly at Marv, who blinked dumbly back.

“Speaking of the mission, it’s changed slightly...”

 

\--------------------

 

That night the group made their way over to The Roadhouse, which Ellen had decided to close early for a family dinner. Gabriel immediately made his way to the back of house to help Ellen prepare the desserts, dragging Sam along with him. Balthazar, Crowley, Dean and Castiel made themselves comfortable at the bar, where the strong looking bartender had his back turned to them. It took the bartender a minute to finish his project before he turned around to greet his guest with a beautiful wide smile.

“Howdy ya’ll,” he drawled in a deep southern accent; Dean just about fell off his barstool, “th’ name’s Benny.”

Castiel shot a curious look at Dean, who was now a pasty white. “Dean?”

Benny’s attention shot straight towards the name, “Well I’ll be! If it isn’t the one and only Mr. Dean Winchester? How have you been love? Long time no see, I think the last time I ever heard from you was the night when we-”

“Yeah it’s been a while,” Dean cut him off, glaring at him in a silent plea to keep his mouth shut. 

Balthazar caught the looks being exchanged between Dean and Benny and the look of concern on Castiel’s face.

“The night when you what? C’mon don’t be secretive. Secrets are no fun after all.” He chimed innocently, partly regretting it when Dean’s face turned to anguish.

The group was silent for a moment, the only sound was that of faint clinking from the kitchen.

“Dean?” Castiel whispered, resting his hand on Dean’s shoulder. Dean let out a sigh and turned to Castiel, taking both of the other man’s hands in his own.

“Benny and I met before my dad died. He would serve me booze even though I was underage and eventually we got to the point where whenever I was in town to visit Bobby, he and I would hook up.”

Castiel squeezed Dean’s hands gently, encouraging him to continue. Dean sighed and continued. 

“I started coming around more for the sex than the alcohol, and then one day... I realized that I had let my emotions enter the situation. I’m not good with emotions, and up until that day I had never really been in love.”

“So that’s why you jus’ up and disappeared, because you fell in love with me?” Benny chuckled and rested a hand on Dean’s shoulder, “You shoulda jus’ said something. I don’t just go around having sex with anyone who walks in looking for a good fuck you know.” 

Dean stared at Benny, his cheeks bright red. His attention shot straight back to Castiel however when suddenly the warden snapped his hands away and sat rigid, his eyes shooting daggers at the newly uncomfortable bartender. 

“Cas, listen to me,” Dean pleaded, cupping Castiel’s face and gently turning it towards Dean’s own. “That was back then. Back when I had a hit list and severe daddy issues. I’m not the same man I was. All I ever did with Benny was fool around, as soon as my feelings showed up, the rest of me got the hell out of dodge. I haven’t seen, spoken to, or heard from him in five years. And I never had any intention of running into him.”

“But you knew he worked at The Roadhouse.” Castiel accused, settling his steely gaze on Dean. 

“No, I knew he worked at The Roadhouse five years ago. I also knew that five years ago he started making plans to move back to Texas. I assumed he’d gone through with those plans. Otherwise I swear I would have told you before you had to hear it from anyone else.” Dean stroked his thumb across Castiel’s cheek, “I love you Castiel Novak, only you. No one else. I promise that I will love you and only you until the day I die.”

Castiel still looked unsure, even as Dean leaned forward and placed a gentle kiss on his slightly chapped lips. “Benny was fun,” Dean murmured, “but he’ll never be as perfect as you.”

“Ouch, I am standin’ right here you know. Might want to warn a brother before you go insulting his performance.” Benny huffed mockingly, Castiel thought he heard some real pain hidden in the words, but he said nothing. Instead he pulled Dean forward and kissed him again, publicly marking Dean as his. Making sure Benny knew that he had no longer had any claim over the beautiful green eyed man. 

Balthazar and Crowley watched amusedly, clearly curious to see what would happen next. When it was clear that there would be no fighting, they excused themselves and disappeared into one of the back rooms.

“Where did they run off to?” Charlie asked, wandering over to the bar and plopping down on the stool next to Cas.

Jo came over too and sat down on the stool next to Dean, “I don’t think we really want to know,” she answered, waggling her eyebrows and winking at Charlie who smirked knowingly. “Benny, good to have you back.”

“Thanks darlin, not sure how long I’m gunna be around though. I’m thinking about moving back south.”

“Why?” Dean asked, “Stay a while, kick back and lets catch up.”

Benny smiled and shook his head, “I don’t know Dean-o, I don’t have that much money left and I sold my apartment already, I’m living in a motel right now and money talkin’, it would just be better for me to make the move now.”

 “Well you could always shack up with us at Bobby’s. I’m sure he wouldn’t mind. You’d be sleeping on a couch though.”

Benny chuckled, “that actually might be very nice. And a couch will be just fine, as you know I can sleep on just about anything and in just about any position.” When he winked at an already blushing Dean, Castiel felt his stomach sink to his feet. 

Cas hurled himself off the barstool and strode quickly to the door, slamming it behind him on his way out. He faintly heard Dean calling his name, but his feet were on a mission to get him out. Somewhere, anywhere was fine, as long as Benny wasn’t there.

_What the hell was that all about? They could have practiced a little more finesse! So they slept together a long time ago, why does anyone else need to know that? And why is Dean offering Benny a couch?_  Castiel fumed, fists clenched tightly, shoved deep into his pockets.  _And the way they were looking at each other. What if while Benny is staying with us, Dean decides that he likes Benny more then he likes me? No. That will never happen... Dean loves me. He does love me doesn’t he?_  “DAMN IT!” Castiel kicked the ground as hard as he could, dust flew up from the ground and slowly settled back. He climbed the steps to Bobby’s house and sat down on the top one; he relaxed all his muscles and schlumped forwards.  _Dean does love me, that’s not the real question._  He sighed, “The real question is; does he love Benny more?

 

**Notes for the Chapter:**

> The green eyed monster being jealousy....


	23. Chapter 23

**Summary for the Chapter:**

> In which Jealous!Cas makes another appearance and Benny continues to intrude.
> 
> Also, what the fuck.
> 
> Also, please read the Chapter notes.

**Notes for the Chapter:**

> Okay okay okay, so here's the thing guys, I totally didn't realize that I hadn't posted since November, I AM SO SORRY!! This chapter is unedited because I panicked and decided just to get this out here for you all so I apologize for any spelling/grammatical errors! Both Meg (my darling editor) and I have been extremely busy, that is why this has not been kept up very well. I did however just quit one of my jobs so I will start writing more. My goal is to have this fic completed by the end of this year. I am going through and reading all of your comments and I just wanted to say thank you so much for all of your love and support, if you were here through any of the hellatuses, I am sorry and I am so happy to see you again! Meg and I are going to try and work out a new schedule so that this thing posts more regularly. I love each and every one of you and I am going to try and incorporate some ideas that you comment into the fic so feel free to comment away and I'll see what I can do if it fits in with the story (ie. someone has requested a chapter focusing on Crowley and Balthazar, I am currently in the middle of writing CH25 but I'll see what I can do in CH26) LOVE TO YOU ALL AND I'M SORRY FOR THE HEARTACHE!!

Gadreel was an annoying little fuck, and Marv was more then done with his shit. 

It seemed like every time Marv tried to get anything done, Gadreel would be right there to counteract his attempt. Any progress had come to a complete stand still and the two men were getting nowhere fast. It had been a week since they had been paired together and all they had accomplished was getting on each other's nerves.

“Listen assface, this is my mission, I’m in charge. Dick only assigned you here to keep an eye on me, but if you don’t let me get my job done, we’ll both be in for it,” Marv huffed, “Meanwhile, our targets are getting more and more comfortable with their freedom, if I were in their shoes, I’d have already started planning to get as far away from Folsom as possible. They won’t want to stay here forever and it’s only so long before someone realizes that whatever corpses replaced the Winchesters, aren’t really them. Stop sabotaging my plans!”

Gadreel scowled back, arm folded over his chest, “Dick assigned me to make sure that the job got done right. I don’t see how lurking by the windowsills is going to get anything done, other then get us shot once someone notices. If we want to get inside, we need to break the lowest level, the least suspecting.”

“What are you talking about?”

“The Roadhouse. If we find an in with someone there, we’re in with the group.” Gadreel explained patiently. “If we’re in the group, we can learn anything and everything about them without having to lurk and act suspicious.”

Marv rolled his eyes, “Do you really think that they’ll just accept us? Think about it, why would they ever even think about letting us in? Just because all of the sudden we’re regulars? Besides, Balthazar might recognize me from Kitsune Pond. How will that not raise suspicion?”

Gadreel thought for a moment, “I might have a plan, but I need you to trust me for a little while. Worse comes to worse, it doesn’t work and we can try something different.”

Marv looked at him suspiciously and said after a minute of consideration, “What’s the plan?”

Marv shuffled his feet unhappily as he sat next to Gadreel, back in the office of Dick Roman, who sat across from them silently, processing the request.

“Let me get this straight,” Dick said, after ten minutes of complete silence, “you two want me to release three members of the Italian Mafia to help you catch their own Leader? Do you think I’m stupid? What happens when they team up with their leader? Are you two going to stop them?”

A tall man with blue eyes and salt and pepper hair stepped forward from the shadows, Marv jumped slightly, realizing that they hadn’t been alone.

“I’ll go with them. If the prisoners need to be taken care of, I will personally deal with them.” He said in a bored tone. Roman beamed up at him.

“Cain! What a splendid idea. It’s decided then,” he clapped his hands together, “Cain will accompany you two and make sure that Azazel, Dr. Green and Roger keep in line.” He turned to Chet who was standing by the door, “Chet, go get the prisoners.”

Chet nodded and then was gone. He returned a few minutes later with the men in toe. None of them looked pleased but for some reason, upon seeing Cain they became more at ease. Marv glanced uncomfortably from one face to the next, pleased and worried that Gadreel looked just as uncomfortable with them as he felt. 

“Gentlemen,” Roman announced, “meet Marv and Gadreel. They are in charge of taking down Dean Winchester. You are being given the opportunity to help them. Should you say no, nothing will happen. However, if you say yes, the more helpful you are during the mission, the more time will be taken off of your sentence.” Azazel and his croonies exchanges glances and smirks. 

“What do you need us to do?”

 

\----------------

 

Dean and Castiel were still not on good terms. Benny had been living with them at Bobby’s for a week now and it was putting pressure on Dean and Cas is all the wrong ways. Dean was prone to staying up late with Benny, sitting on the couch and catching up. It was never on purpose, one minute they were just finishing up dinner and suddenly it was 4am. Last night Castiel had woken up from a nightmare at 2am and turned over to find Dean’s side of the bed empty and cold. He had meandered downstairs only to find Benny and Dean sitting comfortably on the couch, thighs touching, Benny leaned closer to Dean and muttered something, careful to keep his voice low for fear of waking anyone up. Dean had laughed and Castiel’s heart sunk at the look on Benny’s face. He slunk back up the stairs, crawled back into bed and cried himself to sleep. Dean had crawled silently into bed around 5, Cas had pretended to still be asleep. He lay in silence as Dean got comfortable, arm draped lazily around Castiel’s waist, his mouth pressed up against the back of Cas’ neck in a soft kiss. 

Castiel had woken up a couple hours later and gone jogging with Sam. He loved the familiar burn in his thighs and the crisp air filling his lungs. When they arrived back at Bobby’s, Castiel looked into the kitchen window as they made their way around to the front door. Dean was sitting at the table, clutching a cup of coffee. Sam gently nudged Castiel’s shoulder, “dude, could you be any more obvious?” Castiel smiled sheepishly and peered back into the window. The smile slid from his face as he watched Benny shuffle sleepily into the kitchen, and plop down next to Dean, resting his head on Dean’s shoulder. 

“C’mon Cas, it doesn’t mean anything. They are just old friends is all,” Sam said. Castiel nodded, but wasn’t blind to the hint of uncertainty that laced the younger Winchester’s words. 

When the two men entered the kitchen, Dean stood up and walked over to the sweaty warden, wrapping his arms tightly around the dark haired man and kissing him soundly on the lips. 

“Morning babe,” he mumbled, lips still pressed against lips. Castiel said nothing, but cautiously wrapped his arms around Dean’s waist. Dean smiled at the gesture, “You had me worried, I woke up this morning to a cold bed. I didn’t know where you had gone.” 

Castiel sighed and pulled away, “I went on a run with your brother. I can assure you that I was fine.”

Dean stepped forward slightly to capture Castiel in his arms again, but the warden stepped away and moved quickly to the other side of the room. 

“Cas?”

“If you’ll excuse me,” Castiel said as he walked towards the stairs, “I’m in need of a shower.”

Dean followed him to the bathroom but Castiel blocked the door, “Dean, I just need a little privacy okay?” He spat, before closing the door in the older Winchester’s face. 

_This is not the way to keep Dean out of Benny’s arms,_ he scolded himself, _perhaps you should just let him shower with you. At least then you’ll know that he’s not with that bar slut._ Castiel ground his teeth in frustration as he turned on the shower. His inner turmoil continued as he stripped down. When he looked in the mirror, his eyes raked over his lean figure. Hickies were scattered down his torso and there were light scratch mark on his hip bones from when he and Dean got just a little too rough. Tears welled up in his eyes and he shook his head in an attempt to clear his jealous mind. He stepped into the shower without testing the water and cringed when the scalding water hit his tender flesh. He made no effort to change the temperature and stood still as the water attacked his skin, turning his whole body red and numb. Castiel thought about Dean, downstairs with Benny. How the two of them looked at each other and his heart broke. He sank to his knees and buried his face in his hands. _Maybe it’s all for the best,_ he though his chest rapidly raising and falling as he sobbed silently on cool tile shower floor, the scalding water still beating down on his back. _Dean is a murderer and he was your prisoner. Why on earth did you think this could possibly have a happy ending?_ He stayed in there until long after the water turned icy. Shivering he dragged himself from the floor and turned off the water. He wrapped the cotton towel loosely around his waist, it hung low enough to show his sharp hip bones and the scratches that littered them. If he had looked in the mirror he would have seen the dark circles under his eyes and the blue tint to his lips, but he instead ignored the mirror and quietly padded his way down the hall to his bedroom. He opened the door and threw his clothes down next to his side of the bed, closing the door behind him and then falling onto the soft mattress, not bothering fixing the towel when it slipped off him, not caring enough to try and cover himself with something else. He let out a scream into the pillow and he cried until the darkness engulfed him, his body consumed in the desire to make up for all the sleep he’d lost worrying. 

He didn’t notice the man that slid out from underneath the bed a few minutes later and snuck out the door, nor did he notice the camera the man had left attached on the wall in the corner of the room.

When Castiel woke up he was freezing. His limbs felt heavy and he couldn’t bring himself to move. He was vaguely aware of the sound of footsteps nearing the room, but he still didn’t move. 

“Cas?” Dean’s voice wafted through the door, “Hey Cas, mind if I come in?”

Castiel didn’t answer and instead sunk lower into the bed. He heard the door open and Dean inhale sharply. Then blankets were being thrown on top of him and he was being pulled up into Dean’s arms. Castiel let his body be moved around. Dean was warm and the blankets were soft. He curled up into himself and felt Dean run his hand over his back comfortingly. 

“Castiel, what’s going on?” Dean asked, voice gentle. “You’ve been acting strange lately. Shutting me out, and you’ve been quite rude to Benny,”

At the mention of Benny’s name, Castiel pushed away from Dean, locking eyes with him. “Benny? Is that why you care? Because I’ve been rude to Benny?” Cas spat, his voice full of contempt.

“What? No! Cas don’t be ridiculous! I care because I lo-”  


“Don’t.” Castiel snarled. “Don’t say that you love me. Not when you spend all of your free time with him. You didn’t come to bed last night till 5am, and this morning I saw you two getting all comfy at the table. I’m not blind Dean and I know you two have history. I know the way he looks at you, like you’re an oasis and he’s a severely dehydrated camel.”

“...a camel?”

“Yes. Because Camel’s are intrusive and they smell bad.”

Dean stared at Castiel for a moment before his lips turned up into a smile and he started laughing. Castiel stared back, getting more and more mad by the second.

“C-Castiel,” Dean choked out between laughter, “I promise there is nothing going on with me and that C-C-Camel!” tears were now streaming down his face from laughing so hard.

With one solid swing Castiel punched Dean square in the jaw, causing Dean to yelp in surprise and tumble off the bed. 

“What the fuck!” Dean cursed, getting back up and gently holding his jaw.

Castiel stood up on the bed, “I COULD SAY THE SAME THING!” he shouted, “DEAN WINCHESTER YOU ARE A COMPLETE ASS!”

Dean stared at Castiel for a moment before growling and tackling the naked warden back down onto the bed, firmly pinning him down. 

“Castiel Novak calm the fuck down.” Dean hissed, crawling on top of the writhing man. Castiel went to punch Dean again but Dean caught his fist before it could do any damage. “Dammit Cas!” He huffed as he grabbed Castiel’s wrists and pinned them above his head. Castiel still struggled, trying to get away. 

“Stop. Moving.” Dean growled, holding both of Castiel’s wrists in one hand and using his other hand to remove his belt. He used the belt to tie Castiel’s wrists securely to the bedpost. Dean cupped Castiel’s face in his hands, “hey, Cas come on, look at me. What’s wrong with you?”

Castiel was livid, _how DARE he tie me up like this?_ “Let. Me. Go.” He snarled, bucking up his hips in an attempt to throw Dean off of him. 

“Not until you tell me everything. Like what the hell is going on with you. You know that I don’t like Benny like that.” Dean countered, hands still holding Castiel’s face towards his own, forcing the other man to look at him.

The warden sneered, “It’s not about what you feel Dean. It’s about what Benny does. Are you really too stupid to see that he’s still in love with you. He’s been trying to get you into bed with him from the moment he got back. And you haven’t been doing anything to dissuade him. For all I know, you were up so late last night because you were fucking him instead!”

Dean coiled away at that as if Castiel had punched him again. Cas kicked his legs again and sent Dean flying to the floor. He let out a triumphant huff and pulled again on his restraints. Dean slowly stood back up and silently watched Castiel struggle. 

“He wanted to.” Dean admitted quietly, causing Castiel to freeze up immediately. Dean sighed and sat down on the edge of the bed, he ran his hand across his face and then through his hair. “Benny, he wanted to do stuff last night. I didn’t realize what he was planning until he started to kiss my neck. We were watching a movie and I had had a little too much to drink, he was laying on the couch and I was leaning back on him, I knew I was already pushing boundaries but you’ve been so distant lately and I just needed someone to hold me. Nothing inappropriate was happening and I was drifting off when I felt lips against my neck. In my half-conscious state I thought it was you, so I didn’t move away. He took that as approval to continue. I didn’t realize it wasn’t you until his tongue was in my mouth.”

Castiel felt like he was going to throw up, he scrunched his eyes closed, trying not to picture the scene laid out before him. 

“As soon as I realized who I was really with I pulled away. He tried to convince me to stay and I yelled at him. I was really mean and I felt kinda bad but Cas, I don’t want to be with anyone but you.” 

“So then why didn’t you push him away this morning at the table?” Castiel questioned, his voice scratchy from crying and yelling. 

Dean sighed, “I thought that was his way of apologizing for last night. And after I’d been so mean to him I couldn’t bring myself to shove him away. Cas, believe me, if I had known how upset you already were with him, I wouldn’t have let him near me this morning.”

Castiel caught Dean’s eyes, “were you going to tell me?” He whispered, “did you have any plans to tell me about what happened last night?”

Dean exhaled and stroked Castiel’s cheek softly, “Yes. I was going to tell you this morning when we woke up. But you were already gone. Then I was going to tell you when you got home but you said you needed some privacy. If I hadn’t told you now I would have told you tonight in bed. Cas, Benny and I have history yes, but that’s all it is. I would love for him to be a friend, but if he can’t keep it in his pants then I’m done with him. I only want you.”

The bound warden shuttered as his prisoner’s lips captured his own. He moaned into the touch and savored the taste of Dean’s tongue. When Dean untied his hands, Castiel wrapped his arms around the younger man’s neck and pulled him closer. He flipped them over so that Dean was on his back below Castiel, his hands holding tightly to the warden’s naked waist. 

“Castiel Novak, you drive me crazy.” Dean whimpered and Castiel growled possessively, claiming Dean’s lips in a frenzy of need and ownership.

The camera in the corner of the room hummed softly unnoticed as it zoomed in on the two men. 


	24. Chapter 24

**Summary for the Chapter:**

> In which Benny is a dick and Dean (finally) lashes out.

**Notes for the Chapter:**

> Meg and I have been super busy lately so this chapter is unedited. I will post the edited chapter once it's finished, but I liked this chapter a lot and didn't want to keep you guys waiting too long <3
> 
> P.S. Please leave comments and kudos so that I know this fic is still worth me spending time on, I rarely will go back and read what I wrote (unless it's just to edit it) So I don't actually know what it's like to read this whole thing as a story, there are so many deleted scenes and alternate chapters that I wrote and then deleted because I didn't like them/they didn't fit, so sometimes I forget what I actually did publish. (ヾ;￣▽￣)ヾ
> 
> Okay so there is all of that, ENJOY THE CHAPTER!

The next morning rain pelted the window and they sky remained decidedly grey. At breakfast Cas made sure to trap Dean between himself and Bobby, effectively cutting any potential contact from Benny. This earned a smirk from Sam and an amused eye roll from Bobby. When Benny walked in his eyes immediately focused in on Dean.

“Mornin’ brotha,” he yawned, raising his arms slightly to show a bit of tanned stomach. Castiel glared down at his coffee and tried to hide his frustration by taking a long sip of the scalding beverage. 

“Morning,” Dean replied, casually slipping his arm across Castiel’s shoulder and pulling the fuming warden close. “Sleep well?” 

Benny’s eyes flickered over to Castiel for a moment before returning to Dean, “like a bug snug in a rug. You?”

Dean moved Castiel’s face towards his and smiled seductively, “We didn’t get much sleep last night,” he said, pulling Cas towards him and kissing him slowly and deeply. Cas let himself melt into Dean’s arms, humming softly, partly just to piss Benny off. 

“God you two, get a room!” Sam huffed, Bobby grunted in agreement. Gabriel walked into the room and let out a wolf whistle before climbing into Sam’s lap and attacking the younger Winchester’s mouth with his own. Sam let out a surprised yip but was quick to wrap his arms around the con-artists waist. 

“Speaking of getting a room...” Gabriel hinted, smirking when Sam groaned and stood up, holding the older man close to him, Gabe wrapped his legs around Sam’s waist and tugged lightly on the younger man’s hair, attacking his exposed neck with gentle nips and kisses. 

“Excuse us,” Sam muttered to the room before stumbling out distractedly.

The rest of the room watched in silence as the two men disappeared from the doorway, there was a scuffle on the stairway followed by a thud. 

“What the bloody Hell?”

“Well they sure have made up and are getting busy I see,” Balthazar said, entered the room smirking, followed by an unamused Crowley. 

“Squirrel, please do at least attempt to control your giant moose of a brother. We were almost squished!” Crowley huffed, taking the seat Sam had occupied a minute ago, perfectly content with letting Balthazar fetch the coffee. Dean simply rolled his eyes and turned his attention back to Castiel.

“So, what are we going to do today angel?” He asked, cupping Castiel’s cheek and stroking him gently with his thumb. 

Cas smiled, “movie marathon?” He suggested, leaning into the touch.

“Sounds perfect,” Dean replied, “there’s a TV in our room, what do you say to grabbing some sustenance and the two of us spending the movie marathon in bed? Seems like a good day for it.”

Castiel planted a kiss on Dean’s lips and nodded. “Well it’s settled then,” Dean said, addressing the rest of the room, if any of you sons of bitches need anything from Castiel or myself, keep it to yourself until tomorrow. For today we are going to have a quiet day in.”

Balthazar grinned smugly, “I believe the term you’re looking for is ‘Netflix and Chill’.”

Dean shot him a confused look and Castiel fixed Balthazar with his best glare. 

“Netflix and...”

“C’mon Dean, lets go figure out what we’re going to watch.” 

Dean rose slowly from his seat and grabbed Castiel’s hand, “C’mon Angel,” he smiled, pulling Castiel gently towards the living room. 

“I’m no Angel Dean, you know that.” Cas huffed amusedly.

“You’re my Angel. You saved me. Pulled me from the deepest pits of Hell. Raised me from Perdition.” Dean said dramatically.

Cas rolled his eyes and playfully shoved Dean away. “Stop talking now Winchester, or I might have to smite you.”

Dean flopped down onto the couch and waggled his eyebrows. “So what movie are we watching?”

“Well that all depends, do you have a preference?”

“Cas, anything you pick is totally fine with me.”

Castiel looked slyly over at Dean, “Can we watch a marathon?”

“Anything you pick is totally fine with me.”

Castiel smirked, popped in a movie and crawled onto the couch, lifting his legs up and leaning against Dean’s chest. “Just remember that you love me.”

Three and a half hours and twenty-two songs later Dean was regretting his decision to agree to a marathon of whatever Castiel wanted. 

“Remember that you love me Dean,” Cas sang as he popped the third High School Musical into the DVD player. Dean groaned and slid down on the couch. “Please Cas, this is torture.”

“Consider it the remainder of your prison sentence,” Castiel retorted. Dean huffed and rolled his eyes, pulling the warden close to him and hugging him tightly. “I’d almost rather be in prison,” Dean huffed into Cas’ neck. Castiel pushed him away and chuckled. “Liar.”

Benny watched the whole exchange from the doorway, he watched the way Dean’s hands grabbed at the wardens hips as he pulled him closer, the muscular shape of Dean’s body sprawled out on the couch. He noticed that as the movie started, Dean’s eyes didn’t glance towards the screen once, they just studied the man sitting annoyingly close to him. Castiel, the ass, didn’t even seem to notice that Dean was completely smitten, in fact, he didn’t even glance at the beautiful green eyed man. He was completely captured in the movie, and Dean was completely content watching Cas’ mouth as he sang quietly along with every song. Castiel reminded Benny of an annoying pre-teen girl. What grown man decides to watch all the High School Musical movies while sitting in the lap of a convicted felon? Their whole relationship just seemed like a bad joke. Benny huffed and went back into the kitchen, he popped some popcorn and grabbed two beers, unbuttoned his flannel just enough to expose the black v-neck underneath, ruffled his hair and then padded into the living room.

“Hey brotha’, mind if I come watch with ya?” He grinned, sitting down in the recliner closest to Dean. 

“Uh, sure Ben,” Dean replied, shooting the bartender a small smile and tightening his arm around a slightly annoyed Castiel. 

“Brought ya this,” Benny said, handing Dean the beer and setting the popcorn bowl on the coffee table in front of them. “I didn’t think you’d want one Cas man, you don’t really seem like a beer kinda guy.” He said, smiling sheepishly.

Castiel rolled his eyes and turned his attention back to the movie, snuggling closer to Dean. “It’s okay Benny, I’m sure Dean and I can just share. After all, that’s what boyfriends do.”

Dean smiled and handed Cas the beer, “anything for you ‘darling’.” 

Benny plastered on a smile, “How very domestic. Never thought I’d see that from you Dean, you always seemed like the kinda guy who’d never even dream of being tied down. Looks like this one’s got you effectively neutered. You’ll make a great trophy-wife though I’m sure.”

“What the heck are you talking about Benny,” Dean asked, pretending to pay more attention to the TV.

“All I mean is, for the rest of your relationship, you’ll always be the murderous prisoner that got made the warden’s domestic bitch.”

“Benny, I think it’s best if you leave.” Castiel said harshly. Dean was fuming, glaring murderously at the TV as Troy and Gabriella sang in a treehouse. 

“Aw, I didn’t mean to hit a nerve, I was just sayin’ what every one else here is thinkin’.” He smiled sadly, “I just thought you two already knew, it bein’ so blatantly obvious and all.”

“Benny. Out.” Cas growled, looking worriedly at Dean whose fists were clenched to the point that his knuckles were a ghastly white.Benny shrugged and huffed a little, feigning ignorance. “Dean-o, when did truth tellin become a sore subject?”

Dean turned his glare on the bartender, “Benny. Please just, leave me alone.”

“I’m here if you need me,” Benny said, looking Dean directly in the eyes for a moment before turning away and walking through the door. He stopped just outside and listened for a minute to Castiel trying to soothe Dean.

“No one is thinking-”

“Not now Cas.”

“Dean, you just need to know that-”

“I said not now Castiel.”

“... Just listen to me for a moment-”

“DAMMIT CAS! I said not now!” 

Benny slipped into the coat closet just before Dean stormed out of the living room. He watched through the cracked door as Dean drew closer, _‘Shit.’_ Benny pushed himself deeper into the closet, behind as many coats as he could and held his breath as Dean opened the closet door, snatched his jacket and slammed it shut. Benny waited until he heard the front door slam before he snuck out of the closet. He peered into the living room and saw the warden, head in his hands, silently shaking. 

_‘Now’s my chance. This is my time to get Dean by himself.’_ He grinned, Benny quietly made his way out the back door. The first thing he noticed was that Dean’s car was still parked quietly in the driveway. Impulsively Benny slid into the backseat and laid down in the foot-space, covering himself with blankets. Knowing Dean, he wouldn’t want to just drive some truck of Bobby’s. He would need time with Baby. Benny lay there for almost thirty minutes before Dean threw open the door, climbed roughly inside and shut the door. The familiar rumble of the engine shook the car and Dean let out a sigh before he started driving. Benny remained absolutely still the whole ride. One wrong breath and he would be in more shit then he’d ever been in before. They drove for a little over an hour before Dean pulled into a back-alley roadhouse. Benny counted to thirty after Dean left the car before sitting up slowly and letting out a sigh. He made his way inside, careful to sit in a dark booth, out of Dean’s sight but somewhere he could keep an eye on the Winchester. 

“Whiskey please.” Dean gruffes, barely making eye contact with the bartender. 

“Anything for you darlin’” She smiles, hips swaying as she saunters to retrieve a glass, and Dean doesn’t stare. Not even a glance in her direction. Benny watches as Dean downs shot after shot. 

“Got something troublin’ ya sugar?” The bartender asks, for a moment Dean looks up. She has dark hair and light blue eyes, full lips which are currently formed into a seductive smirk. “I am currently living in a house with my boyfriend, my ex-fuck buddy slash first... love I guess, my brother, his boyfriend, his boyfriend’s brother, and his boyfriend’s brother’s... something. So yeah. Right now I got a lot ‘troublin’’ me. Because today, my boyfriend and I were watching these movies and it was sweet and all, something that I don’t usually do, but this man, he makes me do things and say things I used to think I’d never do or say. He makes me feel like I’m more then just some piece of trash. Because when he looks at me I can see it. I can see how much he loves me. At least, I thought I could see it. But then Benny, that’s my ex, Benny comes in today and interrupts our movie date and says these things. How Cas, my boyfriend, is only with me because he’s proving that he can, tame me or something I guess. Benny says he’s not really in love with me and you know what, Cas doesn’t even try to correct him. He just tells Benny to leave and when Benny does and I look at Cas, all I see is pity.” Dean downs two more shots before continuing, “he pities me. He fucking pities me. And that pity makes me question our whole relationship. And I fucking hate it. I hate doubting him. He’s the only thing in my life that’s been good. I mean, really really good. Not just good for a while good. We had our differences at the beginning but there wasn’t ever a minute that I hated or disliked him. He’s the person who I thought didn’t have a hidden agenda. I though he was sincere. But now I don’t know.” Dean threw back three more shots and the bartender shot him a worried look. “Pour me another double.”

“Here’s the deal, feel free to drink as much as you want, but I’m not letting you drive home if you take another shot. There’s a spare room in the back with a little mattress. The owner sometimes sleeps there when he and his wife have issues, the rest of the time it’s used for people who are too drunk to drive. If you take another shot you’re spending the night. Understood?”

Dean rolled his eyes and motioned for her to pour. 

“Keys.” She demanded. Dean glared at her for a moment before reaching into his pocket and pulling out his keys, he threw them on the bar top and she hung them on a rack before turning around and pouring Dean a double scotch. Three of those later and Dean could hardly keep his head up straight. 

“Allright mister,” the bartender sighed, “I think it’s time for you to be done. Let’s get you into that bed.

“ Look, murssis. I promise tha’ I’mnotreallthatdrunk.” He drawled, batting his lashes. She shook her head and helped him stand, guiding him slowly towards the backroom while he muttered drunken slurs.

She came out a minute later and went to greet two burly gentlemen who had seated themselves at the bar. Benny took his chance to sneak into the backroom.

The room was dimly lit but very well kept aside from a single cobweb in one of the upper corners. Dean lay on a Queen sized mattress in the corner of the room, moonlight streamed through the window and fell gently across the mans face. Benny moved forward carefully, nearing Dean. He removed his coat and shirt as he neared his resting friend, slipping of his shoes before crawling onto the matress. Dean blinked his eyes open dazedly, “Benny? What are you-”

“Shhhhh,” Benny cooed, wrapping his arms around Dean’s waist and pulling him close. “Just relax, let me take care of you.”

Dean shook his head and pushed on Benny’s chest in a feeble attempt to put some distance between them. Benny swung a leg over Dean’s and pushed on Dean’s shoulder so that Dean was underneath him, trapped the bartenders strong body and his own intoxication. 

“Cas,” Dean moaned, still weakly trying to push Benny off of him.

“Dean, brotha, weren’t you listening earlier? That warden, he’s just with you to make a point. To prove that he’s better. He doesn’t love you. Think about it, if he loved you, wouldn’t he be the one here right now?”

Dean shook his head, a tear fell onto his cheek and slid slowly down. Benny leaned in and captured it with his lips. He kissed Dean’s cheekbone, then his jawline, his adam’s apple, when Benny turned his attention to the place where Dean’s jaw met his neck, he started to suck and lick and nip.He repeated this across Dean’s neck, purple bruises formed in neat little circles and ovals, marking Dean. The elder Winchester cantered his hips and rocked up, trying to find friction, begging for relief. Benny could taste the salt from the tears still cascading down Dean’s face as he moved towards the man’s mouth. When their lips met, Dean broke out into a sob. Benny kissed him deeply, swallowing his cries.

“Wh-why? He loves me. He said he does,” Dean cried as Benny moved his hand to grope at Dean’s semi-hard member. 

“He’s a liar Dean. But it’s okay, I’m here.” Benny purred, licking the tears away and unbuttoning Dean’s pants, pulling them down to expose Dean completely. He removed his own pants and retrieved the bottle of lube he had taken from the glovebox of Dean’s car. He carefully worked Dean open, stroking Dean’s hair while he cried. When Benny lined up with Dean’s hole, he paused for a moment.

“Dean,” he whispered, caressing Dean’s face, “Dean, let me help you. Let me help erase Castiel from your mind. Let me love you like you should be loved.”

Dean screwed his eyes shut tight and clenched his jaw, “Castiel loves me.”

Benny growled, “If that were true, he would be hereto...”

“To save me?” Dean looked directly into Benny’s eyes. “You’re going to do this wether or not I agree, so just fuck me already.”

Benny glared at Dean, “That was hurtful brotha’,” he growled, but Dean just rolled his eyes and turned away. “Fine.” Benny said before thrusting roughly, penetrating Dean and forcing himself deep inside. He didn’t give Dean time to adjust before he was pumping himself harshly in and out. Dean cried out in agony, he grabbed onto Benny’s arms and tried to push him away, but Benny heard his cry as one of pleasure and took the fingers digging into his arms as encouragement. He sped up his pace and Dean couldn’t breath. All around him was Benny, the smell the feel the sounds, Benny. He was transported back to all the hotel rooms, all the times Benny had gotten him drunk and then brought him upstairs to have his way with the impressionable teen. The lust confused and translated as love, when present day Benny grabbed Dean’s wrists and used his belt to tie them to the iron headboard Dean recalled the first time Benny had tied him up. Dean had been crying then too, it was their second time together and Dean had been worried that his father would find out. Benny had done his best to comfort him at first, but when he realized that Dean was inconsolable he had removed the pillowcases off of two of the hotel room pillows, using one of them to gag the crying blonde, and the other to tie him down. 

Present Dean struggled against the belt but his mind was too clouded, “Benny, please, Castiel loves me.” Benny pounded harder, setting an impossibly brutal pace. “No Dean,” he growled, “That fuck face of a warden does not love you. Why don’t you see that?”

Dean shook his head and struggled more, trying to dismount Benny from on top of him. Benny sucked another harsh kiss into the nape of Dean’s neck and Dean let out a hiss before going completely limp. When Benny attacked Dean’s lips, Dean sighed and kissed him back, slowly at first, but he soon let his actions be guided by his dick and the alcohol. He rocked back in time with Benny’s thrusts and moaned out, calling Benny’s name. He let himself return to being sixteen and sex crazed. Somewhere in the back of his mind he saw Castiel’s blue eyes, saddened by his infidelity, but he quickly pushed the image away and focused on the feeling of Benny’s dick filling him up. Dean hardly noticed when Benny untied him, instinctively he grabbed onto the back of Benny’s head and pulled him down for a bruising kiss. Dean could feel Benny smirking victoriously as his thrusts became more and more erratic. Benny came hard, hissing Dean’s name, his cum filled Dean’s ass and trickled down his thighs. Dean came quietly, Castiel’s name on the tip of his tongue. 

When Dean woke up, the first thing he noticed was that Benny was laying half on top of him, and that they both were completely naked. The next thing he noticed was how sore he was. If the nudity hadn’t told him enough, the sheer amount of pain his ass was in told him the rest.

“Shit.” he groaned, triggering his migraine. He looked at Benny, sleeping peacefully next to him. _How did we end up here?_ He looked around the room and panicked, nothing was recognizable. It looked vaguely familiar but they weren’t at Bobby’s. Dean shifted his position and then froze, he could feel Benny on his thigh, undeniably hard. Benny stirred and opened his eyes slowly. Dean tried to shift away but the older man moved in closer, throwing a leg over Dean’s waist, his erection pressing firmly into Dean’s navel. 

“Mornin’,” Benny drawled, nuzzling his nose into Dean’s jaw, “Ready for a round two?” he asked, smirking as he looked up, his mouth only a breath away from Dean’s.

“Benny, get off me.” Dean said, pushing the other man away as memories from the night before slowly flooded his mind. The pain mixed with pleasure, the guilt. The way Benny had tied him up and fucked him until his will to fight was drained and he had given in.

Benny laughed but complied with Dean’s command. Dean closed his eyes and pressed the heels of his palms on either side of his forehead, willing his headache to go away. 

“You seem tense,” Benny’s voice came from somewhere far away, “just try to relax.” Then there were lips engulfing Dean’s dick. Dean sucked in a gasp and closed his eyes tighter, but he didn’t try to move Benny away. He let himself melt into the mattress as Benny’s lips worked miracles. Benny moved slowly, kissing his inner thighs, nipping them with his teeth occasionally but then soothingly licking the pain away. He buried his nose into the hair at the base of Dean’s dick and took in a deep breath through his nose, pursing his lips on the exhale and sending shivers up Dean’s spine. Dean definitely didn’t replace Benny’s face with Castiel’s when he peeked through his lashes to watch the other man licking hungrily at his slit. He definitely didn’t wish for the eye’s looking up at him to be electric blue. When he grabbed on to Benny’s hair to pull his head down so that he could fuck deeper into the man’s throat, he definitely didn’t close his eyes and picture raven black locks, he imagined the moans coming from Benny as slightly deeper and more gravelly, and a thousand times more tender. Dean definitely didn’t thrust rougher then usual, fucking Benny’s throat as though he were trying to rip it apart. He definitely didn’t force Benny to choke on his dick until he could feel tears streaming down the bartender’s cheeks and falling hotly onto Dean’s thighs. He didn’t revel in seeing Benny red-faced and out of breath, drooling saliva and precum. When an orgasm was finally sucked from him, he definitely didn’t pull Benny’s head down so that the man’s face was pressed up against his groin and Dean’s dick was nestled deep in Benny’s throat. Dean didn’t enjoy the sound of Benny choking as he was forced to swallow down everything Dean gave him while still swallowing around Dean himself. Dean also didn’t force Benny to hold that position, cock shoved down his throat until the other man was fighting for a breath.

It gave Dean and idea and he seductively pulled Benny up to plant a kiss on swollen and abused lips. Benny was still gasping for breath and didn’t argue when Dean flipped them over. Dean planted one last kiss on Benny’s lips before crawling off the bed in search of the belt Benny had used only a few hours ago. When he located it he climbed slowly onto Benny’s lap and tied his hands behind his back, fastening them to the bedpost. Benny chuckled and Dean threw him a wink before attacking his lips in a ferocious kiss. When he felt Benny go lax, Dean moved up.

“Close your eyes and just relax,” Dean cooed, Benny grinned and closed his eyes. “Open your mouth,” Dean said and Benny did what he was told. Dean slid his dick back through Benny’s lips and Benny’s eyes shot open in confusion. Dean smiled down at him and thrust deep into his mouth, not stopping until Benny’s face was once again pressed into Dean’s skin. Dean stilled and waited, after a minute Benny started to struggle against his bonds. Dean stayed put. Another minute past and Benny was becoming frantic, Dean felt teeth scrape and he responded by smacking Benny’s head, hard. 

“Now now Benny love, don’t you get it?” Dean purred, running his fingers through Benny’s hair and digging his nails into the man’s skull. “You seem to love my dick. You love it so much, you just can’t leave me alone you want it so bad. You’re my little cock slut. Don’t you find this poetic?” With a quick move, Dean’s thumbs pressed hard against Benny’s jaw, dislocating it with a snap. Tears leaked from Benny’s eyes and he whimpered as Dean sneered down at the choking man, “you love my dick so much, you died sucking it.”

Benny’s eyes widened and he regained his fight to escape, Dean dug both hands into Benny’s skull and held him firmly in place, Dean’s dick so deep in Benny’s throat that it completely blocked his airway. The Winchester reveled in the power of having another human’s fate in the palm of his hand. Dean didn’t remove himself from Benny’s mouth until Benny had become completely still. He stayed in the room for two more hours to make sure that the bartender was dead before he gathered up anything that could tie him to this place. He walked outside and gathered his keys from the rack and left a hundred dollar bill on the bar before walking out and getting into his car. The drive home seemed to take forever, every bump in the road shot a bolt of pain up Dean’s ass. When he reached Bobby’s, he slipped quietly upstairs and got into the shower.


	25. Chapter 25

**Summary for the Chapter:**

> In which something with Dean and Cas.  
> Also in which something with Benny and Marv.  
> Also Amara cameo. (She isn't a main and as of now I have no intention of her returning but I wanted to mention her at least once.)

**Notes for the Chapter:**

> This chapter is also unedited. Sorry. Life just decided to take a shit on us recently. I'm working on writing more but it's difficult. I've had this chapter ready for a couple of months but currently I only have the first few pages of the next chapter done and I can't seem to find the right way to write it out. The words aren't flowing like they used to. I'm going to still keep pushing on though. I love you all.
> 
> Thank you so much for all of your kudos and comments, it really means a lot and keeps me remembering to update and force myself to get my creative juices flowing. Support right now means the world and I love reading all of your comments. 
> 
> Love you all.
> 
> -M

Castiel had waited up most of the night, but when it became clear that Dean wasn’t coming home any time soon he meandered up to their room and tried his best to get some sleep. He had left Dean a dozen or so phone calls and a few texts but there was no reply. While not hearing anything from Dean was worrisome, the thing that worried Cas the most was that Benny had seemingly disappeared too. No one had seen him since his rude interruption in the living room. When Cas had told everyone what had happened, he was pleased to discover that he wasn’t the only one getting fed up by Benny’s tactics. Castiel wasn’t sure what time it was when he awoke but the sun was barely peeking over the horizon. He put on his glasses, went downstairs and put the kettle on the stove over a low heat, while he waited for the water to boil, he went back upstairs and took a steamy shower, his mind on Dean.The shower was short but relaxing and by the time he was clean and dried off he could hear the faint whistle of the kettle downstairs. He threw on the dark blue robe Dean had picked out for him and returned to the kitchen to make himself a pot of tea. Carefully he carried the tray back to his bedroom, shutting the door behind him. He picked a book off of the shelf and curled up in the blankets, book in one hand, tea in the other. He had just reached Mr. Collins proposal to Elizabeth when he heard the front door close. He put down his book and listened as heavy footsteps crept up the stairs. A minute later the shower turned on and Castiel let out a sigh. He refreshed his tea and picked his book back up. He reread the same sentence for well over twenty minutes, waiting for the sound of the shower to stop. Castiel snatched his phone from the bedside table and flipped the camera to face him. He ran his fingers through his hair, ruffling it the way he knew Dean liked, he used the sheets to clean his glasses before returning his attention to the troubles of Elizabeth Bennet. 

A few minutes later the bedroom door opened and Castiel looked up to see Dean, the dark grey robe made his eyes pop and his damp hair was spiked. Dean stood there for a moment, staring at Castiel. Cas raised his eyebrows and put his book on the table. 

“Good morning angel,” Dean said, eyes gleaming.

Castiel stretched and let out a dramatic yawn, earning a laugh from the stunning man. The warden patted the mattress next to him, inviting his escapee to join him, Dean willingly obliged and slid into bed, curling up close to Cas, letting the blue-eyed man’s scent fill his nostrils and engulf him completely. Castiel smelled like a distant memory, he smelled like the air before a thunderstorm, earthy and slightly sweet, there was a hint of vanilla on his breath from the cream he used in his tea and Dean relished the soft warmth on his neck every time Castiel exhaled. When Dean closed his eyes visions of Benny, dead on some stranger’s mattress, filled his head and he grinned to himself. Castiel wrapped his arms around Dean and buried his nose in Dean’s hair, inhaling deeply. He loved the smell of Dean but something was off about it today. Something even Dean’s shampoo and conditioner couldn’t hide. Dean still smelled like a bar, slightly more musty then usual. He exhaled and pulled away, resting his cheek on Dean’s head. 

“I missed you last night,” Cas muttered, planting a kiss into Dean’s temple.

“I missed you too. I shouldn’t have left like that.” Dean apologized, moving to look Castiel in the eye. 

Cas sighed and bent slightly to kiss Dean’s nose, “It’s okay, I understand. Benny got into your head, but Dean, you have to know that what he said wasn’t true at all. I’m not using you and no one is trying to prove anything. I am genuinely in love with you. I know it’s a different kind of love, it’s a bit strange but it’s love none the less.” Dean grinned and pressed his nose into the soft spot just under Castiel’s ear, inhaling deeply. 

“Cas, baby, I know that. I just needed some time to clear my mind and get Benny out of it. He’s always been good at pushing my buttons. I love you to, you did nothing wrong.” The Warden let out a long sigh and closed his eyes, enjoying the warmth of Dean. Something still felt off but he pushed it to the back of his mind, choosing to focus instead on his boyfriend who had been missing.

“Dean,” Castiel said after a few minutes of silence.

“Yeah babe?”

“Were you with Benny last night? I’m not mad it’s just that, well he, uhm, he wasn’t here at all last night either but his bike is still outside.”

_Shit._ Dean inwardly cursed. He had completely forgotten about Benny’s motorcycle. _It’s going to be okay though, I’ll just sneak out later and go hide it beneath a car somewhere deep in the junkyard. Thank God discarding abandoned vehicles is Bobby’s profession. No one will ever even have to know anything. I can just say that Benny must have come back to pick it up._

Dean was brought away from his thoughts when Castiel shifted awkwardly underneath him, nodding dazedly as he moved to get out of the bed. Dean realized that he hadn’t answered Castiel’s question and Cas had taken the silence as a conformation.

“Wait, Castiel. I didn’t take Benny with me,” _not knowingly anyways,_ “I went to a bar and got shit-faced because when I’m hurt that’s what I do. The bartender took my keys and made me stay there for the night.” Castiel still looked uncertain but he had stopped trying to get out of bed. Dean knew that he had to chose his words very carefully. “I didn’t make love to anyone last night. You are the only one for me Castiel. I would never get into bed with anyone else.” All of what Dean said was true. He didn’t get into bed with anyone, Benny got into bed with him when he was too intoxicated to properly get rid of the sleazy man. Also, Dean did not make love to Benny last night, Benny had forced himself onto and inside of Dean. He had refused to stop even when Dean had begged him to leave. Dean wrapped his robe tighter around him, making sure to keep his neck covered.

Castiel still seemed uncertain but he moved back to lay with Dean again, this time Dean was the one to hold Castiel close, Cas’ head resting on Dean’s chest, his fingers absentmindedly playing with Dean’s robe. “I trust you.” Castiel whispered after a minute. It was a quiet and raw truth, so full of honesty and openness Dean almost felt bad for manipulating the truth. _He wouldn’t understand,_ reasoned the voice in Dean’s head, _He would never understand what happened last night. He would see it as you betraying him, not you being raped by a maniac. He would see you as a murderer again, he would send you back to Folsom and let Dick Roman do as he pleased and he wouldn’t ever look back. He would stop loving you if he knew._ Dean shuddered and pulled Castiel closer, wanting to cherish the moment while he was still allowed one. The Warden cuddled closer and closed his, sighing in content and letting sleep take over. Dean felt Castiel’s breathing slow to a steady rhythm. He made sure that Castiel was really asleep before he slid silently out of bed and ran downstairs and outside. He quickly located Benny’s bike and loaded it into the back of the pick up truck. He drove to the very back of the junk yard and discarded the bike into a large pile of other broken down and abandoned motorcycles, making sure to throw two other bikes on top of Benny’s to hide it better. He drove back to the house and returned to a still sleeping Castiel. Dean crawled back into their bed and wrapped his arms around the resting man. Cas smiled in his sleep and unconsciously threw his leg over Dean’s, pulling Dean closer. Dean stared at Castiel, memorizing his face, the way his eyelashes gently brushed against his rosy cheeks, how peaceful he looked. The curve of his lips, the organized chaos of the soft hair atop his head. Dean loved Cas like this, he kissed him softly before letting sleep consume him to. 

 

\----

 

Gadreel threw the doors open to the bar and sauntered in, Marv walked in sullenly a few paces behind him. Dick Roman had texted Gadreel that there had been a murder that morning and asked him to check it out before the police took all the evidence away, hoping that they would somehow be able to tie the murder to the Winchesters. Marv of course was extremely bitter that Roman had texted Gadreel and not himself, a fact that he made an incredibly large effort to make clear to the slightly annoyed Gadreel by, in essence, throwing a temper tantrum and following it up by not saying anything to the taller man unless it was biting and full of sarcasm and sass. 

Gadreel quickly and quietly assessed his surroundings while the shorter man pouted behind him. There was an open door leading to a back room with police tape crossing in front of it, two cops were inside the room standing over a dead body, a middle aged man by the look of it. There were two more officers in the corner talking to a petite woman, mid twenties, she has delicate features but her eyes were a piercing tone of blue that Gadreel has sworn he’s seen somewhere else. Her long dark hair curls loosely at the ends, close to her elbows and Gadreel watches her lips as she speaks. He moves silently forward, trying to listen to the conversation at hand.

“I’ve already told you officer, I have no idea who that man is. I didn’t see him at all last night. There was only one man that I knew of who was in that room last night and that is most definitely not him.” She huffed, rolling her eyes.

The shorter cop squinted down at her and held back an irritated huff, “Can you please describe once more for us the man who you did allow to stay in that room?”

The brunette crossed her arms, “I’ve told you at least a dozen times by now, I don’t remember. He was maybe six foot? Nice smile. He said he was going through some rough times at home, he got super smashed, I took his keys and put him to bed, alone, when I closed up he was still here, just him as far as I knew. I went home, went to bed and woke up to seventeen texts and three voicemails from my boss saying that someone got murdered. So here I am. Can we be done now? I’ve never seen this guy until now and as rude as this sounds, I do have better things to do today then repeat my useless information a thousand times to cops who can’t do their jobs well enough to remember what’s written down on the paper in front of them.”

Gadreel smirked and watched as the cops exchanged pissed off glances before telling the witness she was free to leave, but to stay in town in case they needed to question her further. 

She collected her purse from the bar and brushed past Gadreel and Marv without so much as a glance. 

“Stay here.” Gadreel said flippantly to Marv as he turned and followed the girl outside. Marv muttered something angry under his breath but didn’t try to come outside with them.

“Excuse me miss!” Gadreel called, putting on his best worried face, “I’m so sorry to interrupt but have you seen my brother?” He pulled out a picture of Dean and handed it to the girl, “He left home last night and he still hasn’t come back. I’ve been trying to hit up every bar I can to find him but so far no luck. His boyfriend and I are very worried.”

The girl looked at the photo, “Uhm, no sorry. He doesn’t look familiar. The next closest place is probably Rising Sun, it’s south about forty miles. Otherwise if you’re going the opposite direction I think there’s a place called the Roadhouse, that’s about an hour and a half to two hours north depending on how fast you drive.” She handed the photo back to Gadreel and adjusted her purse strap. 

“The Rising Sun you said? Thank you, I’ll go there next. And thank’s for your help. If he happens to show up would you mind giving me a call? We’re really worried.” She nodded as Gadreel scribbled his cell number onto an unused tissue from his pocket. “My name is Sam by the way,” he smiled.

“I’m Amara.”

“Nice to meet you, Amara.” She smiled and turned back to her car. Gadreel watched as she drove away before he turned and walked back into the bar. 

Marv had made his way into the crime scene area, lurking in the shadows. He gagged slightly when he saw the man sprawled out on the bed. When Gadreel came back inside Marv slunk out of the room and made his way over to the other man.

“Benny Lafitte, in the flesh. Just minus the soul.” He smirked, “Dean Winchester’s ex-lover, murdered in the middle of nowhere, just about an hour away from where the escapees made their safehouse? Something smells a just a wee bit fishy.”

“Either Dean killed him, or else Castiel did,” Gadreel nodded, eyes sweeping briefly over the scene. “The girl says she knows nothing, I showed her a picture of Dean and she swore she hasn’t seen him.”

“So then it was our little Angel Warden.”

“That or she was lying. I gave her my number, told her my name was Sam and asked her to call if she saw Dean.” Gadreel suddenly turned on his heel and walked swiftly out of the bar and back to their car. Marv groaned and followed reluctantly, not wanting to get left behind but also not wanting to play follow the jackass any more than what was required.

“We’re not going to report anything to Mr. Roman until we find something useful,” Gadreel stated when they were both in the car, “If he requires any update before then, he will contact us.”

Marv sank into his seat and pulled out his smartphone, taking care to turn the screen away from Gadreel as he opened up the live video footage of Dean and Castiel’s room. This was his secret, something that he would never let Gadreel worm his way into. One day, it would pay off and then Roman would see that Marv truly was the better man. He zoomed in on the two men, watching as Dean slid quietly out of the bed, only to return twenty minutes later, sweating slightly.


	26. Chapter 26

**Summary for the Chapter:**

> Crowthazar anyone?

**Notes for the Chapter:**

> Hello, 'tis I the mysterious vanishing asshole who is really bad at updates.
> 
> 2016 has really sucked for me so far, from losing loved ones to being admitted into a mental ward (which I'm sure by the fact that I'm writing this fic, we should have all seen coming.)
> 
> This chapter was really difficult for me to write because I'm losing motivation to just write smut, but since Crowthazar smut was specifically requested I wanted to give it a chapter. The smut will be taking a break for a while so that I can focus on the actual story line. We still need to figure out what's going on with Dick and Marv and if Cas will discover the truth about what happened during the night Dean spent away. I promise that this is not an abandoned work even if it may seem like it at times. I have the ending all planned out I just need to actually hurry up and get there. 
> 
> PLEASE LEAVE COMMENTS AND KUDOS SO THAT I KNOW THAT PEOPLE ACTUALLY LIKE THIS FIC. I know that it's a little dark and a little off but I needed a fic that was like this and there were only like 3 prison fics when I started writing this monstrosity. So please bear with me.
> 
> Love to you all.
> 
> -M

Crowley liked seeing Sam happy again, but he enjoyed seeing the life return to Gabriel’s eyes even more. After Hester died, both men took it hard. Crowley had lost a wife and a best friend, and Gabriel had lost a sister and partner in crime. Her death had brought them closer together, but neither had ever fully recovered. The day Sam Winchester stumbled into Folsom Prison was one of the first real smiles Crowley had seen on his friends face in years. 

As for Crowley, he swore off love, truly believing that finding someone new would be impossible. But resting here in the arms of his bare-chested, smart-mouthed doctor, he could feel himself letting go and giving in. Hester would always hold a special place in his soul, but suddenly there was room for someone new.

Crowley turned the page of his book and sighed contentedly. The best part of reading a printed book was the satisfying way that the pages on the right would slowly get thinner and thinner, while the left ones would get thicker. He was so enraptured by the work that he barely registered the feathery kisses being pressed lightly against his neck. Out of instinct, he lifted his chin slightly and turned his neck to the side, granting Balthazar more canvas to continue his work. When the doctor gently nipped the con-mans earlobe Crowley let out an amused huff and continued reading. After a few minutes of reading the same line over and over again, trying to block out the strong hand sliding down his torso, Crowley shut the book and set it to the side, leaning his head back and closing his eyes as Balthazar slid his hand underneath the waistband of Crowley’s pajama pants, his fingers wrapping firmly around Crowley’s semi-erect cock. Crowley bit back a moan as Balthazar picked up his pace, nipping and kissing the shorter man’s neck and collarbone. When Balthazar locked his lips around Crowley’s adam’s apple and sucked, Crowley’s hips bucked up involuntarily.

“A-ah, fuck.” Crowley growled when Balthazar sped up his pace, his hand now slick with precum.

“Well I’m certainly endeavoring to, love.” Balthazar purred against his ear, licking the shell before returning his attention to Crowley’s neck. 

“Darling,” Crowley muttered, his breath coming out in short gasps as the hand around his cock tightened, “I mean this with all of my heart, screw you.”

Balthazar laughed and removed his hand completely, Crowley moaned at the lost contact, but the moan was quickly replaced with a sharp intake when Balthazar snaked a leg around his waist and smoothly moved himself so that he was now atop the shorter man. He dipped down and bit Crowley’s shoulder hard enough to leave a bruise. Crowley winced at the pain but closed his eyes again when he felt lips kissing and soothing the love bite. He didn’t notice Balthazar removing his pants until the cool air surrounded his dick. 

“Actually love, as much as I do enjoy bottoming, today you will be the one who is screwed.” Balthazar whispered, reveling in the feeling of Crowley coming apart beneath him. The way the con-artist gasped for breath as his cheeks flushed, the doctor bent down and captured Crowley’s lower lip in between his teeth, biting and tugging it gently.

“If you’re going to use your teeth,” Crowley huffed, “then at least use them right.” Balthazar chuckled darkly before biting down hard, Crowley let out a muffled scream as Balthazar released his lip and shoved his tongue down the other mans throat. Crowley’s fingers curved and his nails painted red lines down Balthazar’s bare back causing the taller man to hiss. Balathazar dug his fingers into Crowley’s hips, forcing him to stay still as the doctor wrapped his lips around the trembling con mans dick. He licked the slit slowly, tasting the precum on his tongue. 

Crowley whined and Balthazar pulled away, looking carefully into the shorter mans eyes, “are you okay?” He asked, making sure that Crowley was comfortable before continuing. Crowley huffed an amused laugh and looked back at Balthazar in slight disbelief. 

“Actually doctor, I am feeling a bit feverish.”

Balthazar grinned, “well now, that’s no good at all. Lucky for you I think I have just the right prescription to help you get better. Mind you it may take a little while to set it.”

“Whatever you say doctor.”

Suddenly Balthazar hooked Crowley’s knees over his shoulders and lowered his head slightly, his tongue gently pressing Crowley’s puckered hole. The con man inhaled sharply and grabbed onto the sheets, knuckles turning white as he tried to control his breathing. By the time Balthazar slipped his tongue inside, Crowley was panting and his head was thrown back deep into the pillow. He moved his hips to try and force the doctors tongue deeper but Balthazar smacked his thigh gently and pulled away.

“Patience.”

Crowley growled and then gasped when Balthazar dove back, tongue fucking Crowley’s hole at a glorious pace. Crowley didn’t know how long it was before Balthazar’s tongue was joined by a finger, but soon the con man had two, and then three fingers thrusting deep inside him while the doctors mouth wrapped around Crowley’s dick. One of Balthazar’s fingers found Crowley’s prostate and rubbed roughly over it. Crowley’s whole body spasmed and he let out a wonton moan. For the next five minutes Balthazar continually rubbed against Crowley’s prostate, dragging his fingers in and out roughly while his tongue teased Crowley’s painfully hard member. 

“Balth,” Crowley hissed, “either you start fucking me now or I will pin you to the bed and do it myself.”

Balthazar smirked around Crowley’s cock and pulled of with an obscene pop. His lips came crashing down against Crowley’s and the shorter man slid his fingers through the doctors hair, pulling him closer. Balthazar continued gently opening Crowley up with his fingers before pulling away completely and placing a gentle kiss onto Crowley’s forehead.

“Fuck,” he whispered, gazing down at the man beneath him. “I love you.” He pressed another kiss on the tip of Crowley’s nose and used one arm to prop himself up over Crowley while he gently lined himself up with Crowley’s hole. 

Balthazar moaned at the sight of Crowley’s jaw going lax when the head of the doctors dick slipped past the tight ring of muscle. Balthazar wanted to draw out the initial entrance, he wanted to watch the man he loved come apart more and more with every inch he was subjected to. Crowley let out a small whine and moved his hips in a plea for more and Balthazar smiled as he slid in slowly. Crowley cursed under his breath, his eyes shut and his breathing shallow. 

Balthazar drew back so that only the tip of his dick was still inside Crowley, he pressed forward again, drawing out the feeling of being wrapped up in his lover. Crowley’s ankles hooked together behind Balthazar’s back as the con-artist drew his doctor closer. Their lips met again and their kiss was slow and passionate, matching the pace of Balthazar’s hips. Crowley’s fingers sought purchase in Balthazar’s hair and the taller man groaned at the feeling of neatly trimmed nails gently scraping his skull. 

“Balth,” Crowley breathed out, the word like a prayer, hardly above a whisper. Balthazar’s rhythm faltered and his thrusts came harder. Crowley’s hands found their way to the back of Balthazar’s neck and his legs wrapped tighter around the dominant man’s waist. Balthazar buried his face in the crook of Crowley’s neck, he could feel his hot breath bouncing off the tender skin just above Crowley’s collarbone. 

Balthazar adjusted his angle slightly until Crowley let out a broken gasp and his thighs went rigid with pleasure. The doctor kept the angle, making sure to hit Crowley’s prostate with every thrust. 

“Fuck, fuck, fuck, Balthazar fuck!”

Balthazar moaned and sped up, moving his head so that his lips were right about Crowley’s, their breath mingling as their bodies intertwined. 

“Balthazar, fuck, Balthazar, oh god.I- I- Balth, God, please, yes,” Crowley whined with every thrust. 

Balthazar could feel the heat coiling in his abdomen and he thrust harder, feeding off of the noises coming from the man beneath him. 

“Fergus,” he moaned, his hand moving to cup the other man’s jaw, their foreheads pressing together. “Fergus, I’m so close. Come with me love.” Crowley nodded, his eyes closed and Balthazar caught Crowley’s bottom lip in between his teeth. 

“Come for me Fergus,” Balthazar whispered and Crowley’s body shuddered as hot cum streaked between their bodies, mixing with the sweat and lust. Balthazar felt Crowley’s hole clench as they released and he couldn’t help the whine that was ripped from his throat. He fucked into Crowley slowly, milking out the last of his orgasm as their lips met once more. 

Crowley’s breath was shaky and when the cum started cooling Balthazar forced himself out of bed. He grabbed a clean shirt from their wardrobe and gently cleaned off Crowley, then himself before throwing it into a corner of the room and returning back into the bed. He pulled Crowley close to him and Crowley’s smiled and threw a leg over Balthazar’s. 

“Balth,” Crowley hummed after a while of comfortable silence. 

“Yes darling?”

“I love you too.”

Balthazar smiled and pressed against Crowley’s lips before the pair drifted off, safe and warm in each others embrace. 


	27. Chapter 27

**Summary for the Chapter:**

> In which the damned writer of this fucking fanfiction was a major bag of dicks and literally can't even.
> 
> I hope you enjoy, please leave lots of comments and kudos so that I know people still actually read this damn thing.
> 
> Thank you to everyone who has kept up with this fic and been excited about updates. You are my life source. More content to come. I'm excited to just fucking finish this damn book.

Dean woke with Castiel wrapped around him like an octopus. He grinned and wrapped his arms around the sleeping man’s torso, hugging him softly.

“Cas, baby it’s time to get up,” he cooed softly, his lips brushing softly in Castiel’s hair. Cas let out a tired groan and squeezed Dean, curling himself deeper into Dean’s embrace. Dean chuckled and started absentmindedly tracing abstract shapes into Castiel’s back. Cas arched into the touch and let out a content sleepy sigh.

“C’mon angel,” Dean purred, “let’s go hop in the shower.” Castiel buried his face deeper in Dean’s chest as a reply but let Dean escape his grip. The warden hissed when at the cold when Dean jerked the covers from the bed and deposited them on the floor. He opened his eyes enough to shoot a glare at the grinning blonde.

“You know what will help you warm up Cas, a nice shower.” Castiel rolled his eyes at Dean’s smile and proceeded to roll lazily from the mattress, his bare feet hitting the floor with a thud. The two men made their way across the hall into the bathroom and Castiel stripped down while Dean adjusted the water temperature. Unseen cameras monitoring their every move. 

A few rooms down Sam and Gabriel were settled contently between the sheets, Gabriel absentmindedly changing channels on the TV in their bedroom while Sam flipped through a newspaper, his fingers running through the shorter man's soft golden hair. A silent camera studied them through a small hole in the frame of a picture hanging innocently on the wall.

Across the hall a camera hidden in a clock showed Balthazar and Crowley still asleep, the fan in their bedroom window humming gently, bringing in clean country air from outside. The clock on the wall ticked monotonously counting down the seconds of the last peaceful day the three couples and their friends would have for a long time.

 

\---

 

Marv sat alone in a musty hotel room, flipping through video feeds and taking his time to study and take notes on each man. A pointed tap on the door drew him from his studies. He locked the tablet and shuffled silently to the door, gazing through the peephole at the sinister man on the other end.

“Room Service,” the smooth voice sang through the wood. Marv unlocked the door and moved so that the other man could enter. 

“Azazel. Good to see you again,” he said excitedly, Azazel peered down his nose at the curly haired idiot standing before him. 

“The pleasure is all yours I’m sure,” he sneered, “you said that if I came back I wouldn’t regret it. So this had better be good.” Azazel started pacing around the hotel room, taking in the old stained sheet and rotting wallpaper.

Marv nodded quickly, “yes sir, I completely understand. What if I were to tell you that the Winchester brothers aren’t actually dead?” Azazel froze, his eyebrow raised.

“Say that again,” he hissed, “and know that if you are lying to me I will skin you alive, and feed you each strip of skin I carve off of your worthless body.”

Marv huffed a laugh as his face spread into a confident grin. “Well don’t worry. I have proof. But first, I have a few... demands.”

There was a loud bang as Marv’s head collided with the wall behind him, Azazel’s hand wrapped around his neck, pinning him in place. “Demands?” Azazel hissed, “who the fuck do you think you are, you are in no place to make any demands. Tell me what you know and I won’t kill you.”

Marv choked out a laugh, “I’m not afraid of you. I work for Dick Roman, the only man in the world who strikes fear into the strongest of mafia leaders. So I think you need to take a step back and listen to what I have to say.”

Azazel’s eyes grazed over Marv before he smiled, “well now, looks like you do have a backbone after all.” He let go of Marv with a jerk and crossed calmly over to the chair by the window and sat down. 

“Join me, won’t you? Seems we have business to discuss.”

Marv crossed the room and planted himself in the chair opposite the mafia man. “To start, I need your word that the Italian Mafia and anyone they have under their control will protect me from Dick Roman. The information I have is more than even that slime ball ‘Gadreel’ is aware of. I need to be sure that I’m not going to end up dead for trying to be a part of the winning team.”

“Total immunity and protection, you have my word.” Azazel nodded, “Please continue.”

“Secondly, I’m going to need money. The resources I am spending on this little project would be rather difficult to explain to the big Dick should he chose to look into my bank statements. I want an account under the name ‘Metatron’ that has at least $5,000 added every Thursday. Of course, the more money, the harder I will work.”

“So basically,” Azazel said after a moment of consideration, “you’d like to join the Mafia?”

“No,” the smaller man laughed, “I don’t want to join anything. When this is all over I just want to be able to retire comfortably somewhere far away and safe from Roman and all the utter crap he seems to enjoy subjecting me to. All I want to do is live in peace and read my books, I’m a collector you know.”

“Your terms don’t seem unreasonable, but you can understand I’m sure why I’m still uncertain about agreeing to them.”

“I get it, you want more sound proof,” Marv got up and crossed over to the bed, he lifted up the mattress and pulled out a stack of black and white photographs. He returned to the table and set them down before Azazel.

“These are snapshots from some of the hidden cameras I placed in the house Dean Winchester and his little posse are currently residing in. I’m sure you’ll be interested to see that Dean and Castiel are unusually close, seeing as how rumor at Folsom says that Dean made Castiel his little bitch. If anything, it seems that Dean is the one who got whipped.”

Azazel slowly studied the photos, “What the hell,” he muttered, “When is this photo from?” He held up a picture of Sam and a very much alive Gabriel cuddled up together on a couch.

“I believe that particular picture is from three days ago,” Marv replied, “Did I forget to mention Sam and Dean aren’t the only people back from the dead? I can give you Sam Winchester, Dean Winchester, Fergus Crowley, Gabriel Speight, Castiel Novak and Balthazar Roche. All of whom are currently very much alive.”

The old light bulb flickered in the middle of the room and cast an eerie yellow glow which seemed to gleam from Azazel’s glare. The taller man let out a sneer and then gathered up the pictures, “Well Marv, you have a deal. You have my word that the Italian Mafia will ensure your protection from outsiders and tomorrow morning you will find an envelope taped under the hood of your car containing your new bank account information as well as a cell phone which we will use to contact you. If you double cross us, your protection will be voided and we will come after you. Do you understand?”

“I understand.”

“Now, what other information do you have?”


	28. Chapter 28

**Summary for the Chapter:**

> In which the descent into the darkness begins.

“Hey Char, wait up!” Jo yelled after the fiery redhead who was bounding wildly to the door of Bobby Singers. 

“But Baaaaabe.” Charlie whined, twirling around to face the blonde who laughed and pressed a kiss to Charlie’s cheek. Jo moved the pie she was holding to carry it in one hand, her other hand reached out to take her fiancé's , their brand new engagement rings glinted warmly in the sunlight. When Bobby answered the door he smiled at the pair and moved aside to let them in. Jo released Charlie’s hand and chuckled as the taller woman rushed off to find their black-haired friend. 

“I believe congratulations are in order,” Bobby grinned, taking the pie from Jo and pulling her into a side hug.

“Thanks, Bobby,” Jo smiled, “Actually, there’s something I wanted to ask you.”

“Sure, what’s up?”

“Well,” Jo walked over to the kitchen table and took a seat, motioning for Bobby to join her. He placed the pie on the table and grabbed two beers from the fridge before taking the chair next to her and handing her one of the cold bottles. “Bobby,” She started again, she took a swig of her drink and then continued, “I was hoping you’d give me away at the wedding. Ever since my dad died, and even before he was gone, you’ve been like a second father to me. When you and my mom got together I know I gave you a hard time at first but I was always rooting for you two. I knew that she would never find someone as perfect for her as you are and I can’t imagine anyone else giving me away to my perfect person.”

Bobby blinked a few times and willed the mist from his eyes to disappear, “Idjit,” he muttered as he stood up and pulled Jo into a hug, “of course I’ll give you away sweetheart. Even if we’re not blood-related you’re my daughter. Family don’t end in blood ya know.”

Jo chuckled and nodded, “So I’ve heard,” she replied, hugging him tightly before she pulled away. In synch, they reached over and grabbed their beers and took a swig. Just as they set their beers down Charlie entered the room, dragging behind her a bewildered Castiel. Dean wandered in lazily behind them, an amused grin on his face, he grabbed a beer from the fridge and popped it open. Charlie had her left hand hidden in her jacket pocket and looked at Jo pointedly, signaling for the blonde to do the same. Jo rolled her eyes and complied. 

“Castiel,” Charlie started, dramatically flinging Castiel into one of the chairs and then pushing Dean into the chair beside him. She cleared her throat and moved back to stand in front of Castiel, she placed her right hand on the back of his chair and leaned in close until their faces were inches away from each other.

Castiel opened his mouth to say something but she quickly pressed her index finger to his lips, “No, just listen.” Castiel closed his mouth and raised his eyebrow inquisitively. “So here’s the thing Cassie,” she said, moving to stand next to Jo, “this may come as a shock to you, but it’s time we came out. Jo and I are having sex.” 

Castiel turned red and Dean choked on his mouthful of beer, Jo and Bobby rolled their eyes and grinned. “Believe it or not Charmander,” Dean replied after regaining his composure, “Cas and I were already well aware of that.”

Castiel nodded in agreement, “Dean’s right, you two haven’t exactly been subtle.”

Charlie threw them both a mischievous grin, “Very true,” she sang, “but there is one little thing you don’t know yet. Jo and I aren’t girlfriends anymore.” Cas and Dean exchanged confused glances before returning their attention to the two women in front of them.

“What? What happened?” Castiel asked, his eyes darting between Jo and Charlie, waiting for an explanation.

“Well to be honest Castiel,” Jo replied, “we were just getting a little bored with being girlfriends.” Before Castiel could formulate a response, both girls held out their left hands, showing off the glittering rings adorning their fingers. 

“So we decided to stop dating and get married instead.” Charlie beamed. Castiel stared in shock for a moment before rising to his feet and throwing his arms around his friends. 

“Finally!” He huffed, earning a slap on the arm from Jo. Charlie giggled and pulled back.

“There is one more thing though Cas,” the red head frowned slightly, “As you know, my parents are dead.”

“Same.” Dean chimed in, holding his beer in salute.

Bobby raised an eyebrow at the Winchester, “the difference being Charlie didn’t kill her father,” he snarked.

Dean smirked and nodded in agreement, “well you got me there, old man,” he laughed. Castiel shot him a concerned glance.

“Anyways,” Charlie continued, “Castiel Novak, you are my best friend, besides my soon to be wife , and I was hoping you would give me away at our wedding.” Castiel’s breath hitched and he threw his arms around Charlie’s shoulders, pulling her into his chest. 

“I’d be honored.” He whispered, voice catching in his throat as emotions took over. 

“Idjits,” Bobby huffed and Jo nodded, smiling in spite of herself. 

“Dean,” Charlie said after her and Castiel broke apart, “obviously you can be the flower girl.”

“May wanna give Sammy that role sister,” Dean snorted, “he’s the one with the Rapunzel hair.”

Charlie considered for a moment, “True, but you have the Rapunzel eyes.” 

Castiel laughed and Dean chuckled while he flipped them off. He finished his beer in one long gulp and went to the fridge to grab another. Castiel watched Dean, glancing at the clock which showed it to be only 11:30am. When he caught Dean’s eyes he looked down pointedly at the beer in Dean’s hand and flicked his eyes back to the clock, Dean’s eyes followed but the blonde just shrugged and grinned as he popped the cap off and took a swing.

 

\-------

 

“What do you mean ‘alive and well’?” War hissed, rounding on Azazel.

“What the fuck do you think I mean you ignorant dick face?” Azazel hissed back, standing his ground. He threw a stack of files on the middle of the coffee table before he unbuttoned his suit jacket and sat primly on the leather couch. With a snap of his fingers, he summoned a beautiful young woman dressed in a skimpy maid outfit. She placed a tray full of cups of steaming espresso. She left and returned a moment later with a bottle of Sambuca which she passed to Azazel with a curtsey before returning to the far corner of the room.

War and Pestilence exchanged looks before taking seats in the tall leather armchairs at the ends of the coffee table. Pestilence took up the files and began flipping through them unhurriedly. Azazel smiled to himself as he poured a count of the colorless liquor into his cup. Slowly he returned the bottle to the table and brought his cup to his lips, sipping gingerly.

“Now, if you don’t mind behaving then we can start planning,” his lips curled up into a sly grin as he took another sip of his espresso. 

Pestilence looked up and shot a warning glare at War who snapped his mouth shut and instead prepared his own drink. The white haired man returned his attention to the files in his hands, his nimble fingers rifling through the pages as War glared into his coffee cup. 

“So Dean Winchester raped Castiel, and yet they appear to be currently living in domestic bliss...” Pestilence muttered, “ interesting don’t you agree?”

Azazel nodded, “Notice also that Lucifer’s beloved Samuel seems to be in his own domestic bliss with that whore, Gabriel.”

War cocked an eyebrow and Pestilence handed him the files. 

“Tell me Azazel,” Pestilence started, “If you were brutally raped by someone, would you help them escape from prison and then start dating them?”

Azazel chuckled, “They wouldn’t be alive long enough to escape from prison.”

“Could be Stockholm Syndrome,” War suggested as he put down Castiel and Dean’s file and flipped open Gabriel and Sam’s. 

“True,” Pestilence agreed, “But Castiel was the Warden... Usually, Stockholm Syndrome works the other way around.”

“Maybe Dean didn’t actually complete the task.” Said a dark voice from the door. “Pickle Chips anyone?” The three men rose in unison to greet the elder man.

“Death, old friend,” Azazel smiled, “so glad you could make it.”

“Yes,” said Death as he entered the room, “My apologies with not joining you all in, what do they call it now? ‘The Clink’? Someone had to stay out here and make sure things stayed afloat.” He popped a pickle chip into his mouth, “That and I simply didn’t want to go.” 

The other men chuckled and returned to their seats, Azazel moved aside to make room for Death. 

“As I was saying," Death continued as he took a seat, "perhaps the real reason Castiel is so okay with being romantically involved with Dean Winchester is because Dean never actually raped Castiel.”

“It is a possibility,” War thought, “the only witness was Cain and he even said that he got called away to do a different hall check so he wasn’t able to stay the whole time.”

“In fact, the only proof we have is that Dean had Castiel pinned against the wall. The other video simply showed Castiel crying but that could have very well just been nerves.”

The maid rushed over and placed a fresh cup of espresso before Death, who nodded politely in return.

“Perhaps,” he said, popping another pickle chip into his mouth, “the safest thing to do would simply to force Dean to rape Castiel, but this time with an audience.” The room became silent other than the crunch of the pickle chip in Death’s mouth. Death bent over to retrieve one of the files and squinted at the bright red **_CONFIDENTIAL: Property of Marv_**  that was stamped onto the center. “I’m sure this ‘Marv’ would be willing to assist us.”

 

\----

 

Charlie and Jo left Bobby’s after dinner and drinks, claiming to need to be up early the next morning. Ellen and Bobby wished everyone a good night and then retreated to their room. Crowley and Balthazar washed dishes while Dean, Castiel, and Sam cleaned up the house. Gabriel yawned dramatically and snuck upstairs as soon as no one was looking. 

Castiel was tying up the trash bag when Dean stepped up behind him. The warden smiled as he let himself be crowded against the wall. He hooked his arms around Dean’s neck and chuckled when Dean pressed a tender kiss on his forehead. Dean made his way down to Castiel’s mouth, leaving a trail of warm kisses in his wake. They hummed when their lips met and Castiel threaded his fingers in Dean’s hair, pulling the man closer and deepening their kiss. Dean grabbed the shorter man’s ass and lifted him up, roughly pressing their groins together as he slammed Castiel against the wall, bucking his hips as Castiel wrapped his legs around them. 

“D-Dean,” Cas breathed, “Put me down, I need to take out the trash.”

“Make me,” Dean growled. He licked a stripe up Castiel’s neck and sent a shiver through Castiel’s spine. Castiel groaned and then using as much force as he dared, he pulled Dean’s hair, forcing the Winchester’s head back. Dean grunted in surprise and Castiel used his advantage to latch his lips to Dean’s neck, sucking a dark mark. When he pulled back to admire his work he noticed a sea of marks that he knew he hadn’t placed.

A cold dread set in his stomach. “Dean...”

“Mmm baby, I love it when you mark me,” Dean panted, grinding his erection against Castiel’s flagging one.

“Dean put me down.”

“Like I said, make me.” Dean laughed, pulling back to look at Castiel. Dean immediately stopped at the look on the dark haired man’s face. “Cas? Babe, what’s wrong?”

“Put me down,” Castiel demanded, his eyes steely and his jaw set. Dean obliged and took a step back. 

“Cas, the trash can wait you know, they don’t even pick it up until-”

“Have you been sleeping with someone?”

Dean looked shocked for a minute but quickly came back to himself. “Yes Cas, I’ve been sleeping with you, remember?”

Castiel snorted condescendingly, “I meant besides me. Have you slept with anyone besides me.”

“Cas, you and I have been together every night since I got out.” Dean replied cooly, reaching out to cup Castiel’s jaw, “babe are you feeling okay?”

Castiel’s eyes flicked back down to the slew of hickeys that hadn’t been there a few nights ago. He heard Dean’s breath hitch as Dean realized what Castiel was referring to.

“We weren’t together two nights ago,” he whispered. “The night Benny disappeared...”

Dean took a step forward and watched in dismay as Castiel took a step back, the warden shoved Dean’s hand away from his jaw.

“You had sex with him.”

It wasn’t a question. It was a statement. Castiel knew. 

“Cas, you don’t understand,” Dean started, but that was all the confirmation Castiel needed. 

“Fuck you, Dean Winchester.” He spat as he grabbed the trash and marched out the back door. 

“Cas!” Dean cried after him, “Castiel please just listen to me!” He chased after Castiel but it was too late. Castiel had disappeared somewhere in the piles of junk cars. Dean turned around and made his way to the kitchen.

“Fuck!” He screamed, grabbing an empty beer bottle and throwing it full force at the ground! He stormed past Crowley and Balthazar to the cabinet. He grabbed the bottle of Jack Daniel’s and took a swig, not bothering with a glass. 

“Squirrel?” Crowley asked hesitantly, “What happened?”

“I killed him,” Dean confessed, taking another swig of Jack. “I murdered Benny and hid his motorcycle in the Junk Yard.”

Dean heard the other men gasp but he couldn’t bring himself to care. “That night, the night that he and I got into a fight and I went to the bar. I guess he followed me there or hid in my car or something. I drank a lot that night and the waitress made me stay in this little guest room... I was almost asleep when Benny walked in.” Dean paused and brought the bottle to his lips again, pouring the amber liquid down his throat. “I remember him crawling on top of me and telling me that Castiel didn’t love me and that he did. He told me that if Castiel really loved me he would have been there to save me. Then he- I didn’t have a choice. I couldn’t move, I couldn’t breathe, there was nowhere to go and he tied me to the headboard. So I just laid there and tried to imagine I was a teen again and this was just another fuck session with the hot bartender. But every thrust was like fire, every moan and grunt was laced with guilt. When I woke up the next morning everything hurt. Benny told me to relax and sucked me off. I thrust so hard that he started choking, he was struggling to breathe and that’s when I got the idea.”

“Dean-” Crowley whispered, “what did you do?”

Dean took a long gulp of the Jack and wiped his mouth. “I played the game. I smiled and kissed him and then tied him up, told him it was my turn. I told him to open his mouth, Benny was always such a whore for my dick, then I shoved myself down his throat and dislocated his jaw and just stayed there. My cock blocked his airway and all I had to do was wait for him to suffocate on it. It was too easy. Bastard didn’t even see it coming. Then I just left.”

Balthazar and Crowley stood silent, gaping as Dean downed the rest of the bottle. 

“Cas saw the marks Benny left and he left before I could explain. How am I going to explain? I cheated on him and then murdered someone.” A tear escaped from Dean’s eye and he wiped it away disgusted.

“You didn’t cheat Dean,” Balthazar supplied, moving to sit next to Dean, “that was rape. The sex was not your fault at all. As for the murder... I’m not saying it was the best move, but it’s certainly understandable. With as much as Cassie really hated the guy I’m sure he would understand. You should go purge the booze from your system and then go try to find your boyfriend.”

“But-” 

“Listen, Dean, Castiel is wildly in love with you. Even I noticed that you were getting some special treatment from the Warden when we were locked up. I’m willing to bet that Castiel has always had the hots for you. Do you really want to risk losing what I’m assuming is probably the best thing that has ever happened to you just because some douchy ex-boyfriend tried to get in the way? Do you really want to let Benny win?” Balthazar sat back and handed the empty bottle to Crowley.

“You’re right,” Dean sighed, “I need to find Cas.”

“But first you need to go upstairs and throw up,” Crowley said, taking Dean’s arm and guiding him up the stairs and to the bathroom. When they passed Dean’s bedroom Dean noticed an envelope under the door. 

“Wait,” he muttered, he stooped down and picked it up. In big red letters on the front read **_Dean Winchester._**  Dean ripped it open and pulled out the piece of paper.

 

 

_ Dean, _

_ We know you’re alive. _

_ Seems like Castiel made you his little bitch. _

_ Wasn’t it supposed to be the other way around? _

_ We’re more than happy to break him for you. _

_ Needham Asylum - Fall River, Massachusetts. _

_ You have 24 hours. _

_ Come and get him. _

_ XOXO Metatron _

 

Dean barely made it to the bathtub before he hurled. His stomach felt like iron, his legs failed and his eyes burned. He could hear Sam and Gabriel joining Crowley and Balthazar but he couldn’t make out anything other than “Castiel” and “Kidnapped”.

**Notes for the Chapter:**

> \--- PLEASE READ --- WARNING --- PLEASE READ --- WARNING ---
> 
> Chapter 29, which will be posted tomorrow, is not going to be friendly. I already know the ending of this fic and it's not going to be one of those "happily ever after" fics because that's just not real. Please take the time to refamiliarize yourself with the warnings and the ratings because this fic was never intended to be fluffy. I gave you your domestic (almost) bliss, but now it's time to return to this stories roots. 
> 
> I love you all, please leave comments and kudos, I love hearing from you. <3
> 
> xoxo - IAmSmaugLocked


	29. Chapter 29

**Summary for the Chapter:**

> Please refamiliarize yourself with all the warnings for this fic
> 
> This chapter contains rape.

“Dean!” Sam cried out, but Dean ignored him. He threw his duffle bag into the Impala and slammed the door.

“Dean please,” Sam pleaded, banging on the window, “we need to talk about this!”

Dean slid the keys into the ignition and rolled down his window. “No Sammy, we don’t.”

“Dean-”

“Dammit Sam! They have Cas! Don’t you get it? They have Castiel and I am not wasting any more time.” With that, he sped off.

 

\-----

 

Dean walked down the darkened corridor, “Castiel?”

There was no answer. 

He pulled the note out of his pocket, double checking to once again make sure he was in the right place. Whoever this ‘Metatron’ douche was, he had gone way too far. Fucking with Baby was one thing, but kidnapping the boyfriend of Dean Winchester was a literal death sentence. 

The building was very old, that much was clear by the flickering lights and the cracked tiles. Cobwebs floated in the dimly lit corners and there was a faint echo coming from inside the dusty vents. 

When he rounded the corner, his heart sank. Castiel was laying naked, tied to a dingy bed. The dirty mattress was covered only with drying splotches of blood and the room smelled damp and musty. 

“Cas?” Dean ran over to the unconscious man. Castiel’s wrists had been rubbed raw and infected by the rope, both eyes were black and blue, cuts littered his face and his bottom lip had been split open. Dean whipped out his pocket knife and began to saw furiously at the rope. By the time he heard the footsteps, it was too late.

“Let me go you filthy son-of-a-bitch!” Dean growled at his captor, the response he got sank his heart to his shoes.

“Now now, Winchester, where would be the fun in that?” Azazel crooned. Dean was forced up and shoved around to face Azazel. Behind Azazel stood War and Pestilence. 

“What is this about? What can you possibly want?” Dean sneered

“Unfinished business.” Azazel smiled, “See, we’re not too happy that you lied to us. At first is wasn’t a big deal, simply because as of the moment you made this pretty piece of ass you bitch,” he stroked Castiel’s hair, “you became our leader.” He chuckled darkly, “Imagine Dean, how we felt when we discovered that you did not, in fact, rape him, how you tried but weren’t able to. Let me guess, you couldn’t do it because you love him. Here’s the little problem Winchester, you ran out of time. Don’t worry, we’re going to give you another chance.” Azazel reached under the bed and pulled out a duffle bag, he rummaged through the bag for a minute before pulling out an orange jumpsuit, Dean’s old jumpsuit. 

The man holding him released him and shoved him closer to Azazel, Dean looked back and saw Cain, who was now leering down at him. Azazel shoved the clothes into Dean’s arms.

“Strip.”

Dean wasn’t sure who he was supposed to keep an eye on, Azazel who was standing uncomfortably close to Castiel, Castiel himself, War and Pestilence who were hungrily watching as Dean undressed or Cain who had retreated ominously in the shadows. As soon as Dean was dressed in the familiar jumpsuit, Cain took hold of him again, this time leading him to a chair and tying him down. Azazel reached into the duffle bag again and this time he pulled out Castiel’s warden uniform.

“Don’t touch him,” Dean growled, but Azazel just laughed. “Don’t worry, dress up never was my forte.” He said as he threw the uniform at War and Pestilence. The two men stalked over to the bed and made sure that Dean was watching as they began to defile the unconscious warden. They ran their hands over every inch of exposed skin, taking turns to fondle and grope Castiel’s flaccid dick. 

“You know, I’m sure Dean would prefer his warden to be a little more prepared, don’t you think so?” War chuckled as he reached into the side zipper of the bag and pulled out an old bottle of lube. 

“NO! Don’t touch him!!” Dean shouted, earning a sharp slap across the face from Cain. 

Dean was forced to watch in horror as War lubed up his whole hand and roughly forced two fingers inside Castiel. He harshly pumped his fingers in and out for a minute before shoving in another finger. He turned and twisted his fingers picking up speed until he was slamming them deep inside the ass of the unconscious warden. Dean struggled against his bonds as he cried out Castiel’s name. Praying that if there was any part of Castiel that was awake he would hear Dean and not feel the abomination happening to him. 

Before Dean knew what was happening there was a dick being forcefully shoved in his mouth, he looked up and saw Azazel glaring down at him. 

“If you bite,” the man growled, “I will let War, Pestilence and Cain have their way with Castiel before I personally fuck him with whatever object I want until his insides are torn to shreds.” Dean gulped, forgetting about the dick in his mouth and started choking. Azazel laughed darkly and grabbed a handful of Dean’ hair. 

“Suck.”

Dean went to work, fighting the urge to bite the damn thing off. Azazel tasted dirty, bitter and slightly metallic. When Dean pulled off for a moment to catch his breath, he noticed blood at the base of Azazel’s hard member. He looked up in horror and Azazel grinned knowingly down at him. 

“It’s Castiel’s. I’m afraid we were a little rough on him last night.”

Dean let out a roar and fought again against his bonds, wanting nothing more then to rip off their dicks one by one and force them up the ass of their owners. Azazel slapped him and growled, “now look what you’ve done Dean. Stop fighting me.” 

Dean looked over and saw War, naked from the waist down, brutally pounding into Castiel’s ass while Pestilence fucked the Warden’s mouth.

“Stop,” Dean pleaded, looking up at Azazel. “Please stop, I’ll do anything you want. Just please stop.”

Azazel regarded him for a moment and then called over his shoulders, “finish up boys. Mr. Winchester has finally agreed to our terms.” Dean kept eye contact with Azazel as the older man pressed the tip of his dick against Dean’s lips. Dean parted them and took Azazel in once more. Dean had never been a fan of giving anyone head, until Castiel had told Dean one night that he’d never been sucked off before. Tasting Castiel as he lost all control of himself had quickly become one of Dean’s favorite things. There were some mornings that Dean would wake up before Cas, simply so that Cas would wake up to Dean swallowing him down hungrily. Dean loved the way Castiel’s breath would hitch and his eyes would go wide before rolling back into his skull, his breath coming out in short pants of praise, Dean’s name breathed out on every exhale, cheeks flushed and nipples hard. Dean had taken a few pictures of Castiel in that exact state of dishevelment and bliss. This is what he tried to picture now, as Azazel pounded mercilessly into his mouth, his dick bruising the back of Dean’s throat and the wiry hairs at the base of his member uncomfortably scratching Dean’s tender swollen lips.

Dean looked over at Castiel and realized in horror that when Azazel had said “finish” he meant literally. Dean watched War throw his head back as he shot his load deep inside Castiel’s abused hole. Pestilence had already pulled out but Dean could see cum dripping from the sides of Castiel’s lax mouth. 

He could feel hot tears rolling down his face, a mix of anger, hatred and sorrow. Castiel didn’t deserve this. It should be Dean on that bed. Dean bloody and used. Azazel growled as he came, forcing Dean to swallow him down as he shot hot loads, coating the back of Dean’s throat. “Swallow, and keep sucking” he commanded as he thrust a few more times in and out of Dean’s mouth. Dean did as he was told. When finally Azazel pulled out Dean gasped for breath, he gagged at the sight of a string of saliva and cum still connecting Azazel’s dick to his mouth. Azazel looked down at his dick and then back at Dean.

“Clean it off.” He said, holding it back up in front of Dean’s face.

“Untie me and I will,” Dean panted, his voice raw.

Azazel just laughed, “no Dean. You can lick it clean.”

If Dean never had Azazel’s dick near his face again it would still be too soon, but all it took was one look pointed look over at Castiel from Azazel for Dean to open his mouth again and start licking Azazel’s now flaccid dick clean, the taste of semen, spit and Castiel’s blood making Dean sick. When he had finished Azazel nodded and Cain untied Dean just enough to haul him out of the chair and lead him over to the bed. Pestilence and War had dressed Castiel in his warden uniform.

“Now,” Azazel said, “it’s high time you kept your end of the bargain.”

Dean looked down at Castiel, he gently slid his hand over his lovers back and leaned down to plant a loving kiss in between Castiel’s shoulder blades. “I’m sorry Cas, I’m so sorry.”

Azazel was on him in an instant, wrapping his hand menacingly around Dean’s neck. “This is rape,” he snarled, “not some cute domestic lovers date by the fireplace. This is about you; Dean Winchester, prisoner and murderer, making him; Castiel Novak, warden and pretty boy, your little bitch. No apologies, no love, no holding back. You’ve raped enough people in your time Winchester. He is no different. He is just some piece of scum who needs to be put in his place.”

Dean nodded that he understood and glanced back at the group of men, watching his every move. He didn’t notice Castiel waking up.

Dean tightened the ropes around Castiel’s wrists, “this is rape,” he muttered to himself as he took off the warden's pants to expose his naked ass, Dean spread Castiel’s legs apart, “It mean’s nothing. Castiel is nothing more then just my little warden bitch, he never has been more than that,” silent tears slipped down his cheeks as Dean lined himself up with Castiel’s bloodied hole, “He needs to be put in his place. This is rape.”

Underneath him, a fully conscious Castiel fought back tears as Dean thrust roughly deep inside, sheathing himself fully in one fluid motion. Dean let out a groan and pulled out slowly, Castiel tried to speak but nothing came out. His limbs weren’t working either and he couldn’t feel his hands. There was nothing Castiel could do but cry silently as Dean slammed in and out of him. There was no sign of love or respect, no consent had been given, no tender touch exchanged. Castiel’s heart lay in pieces on the dirty floor next to the empty duffle bag. 

Dean was having a difficult time keeping his emotions out of this, all he wanted to do was to wrap his arms around Castiel and kiss him, promise him that it would all be okay, tell the unconscious man how much he loved him and how he wished it didn’t have to be this way. Tell him how he tried to fight it, how he never wanted this to be the way things were. But he knew it wouldn’t do any good. Castiel couldn’t hear any of it and all that being tender and loving would get right now was disapproval from the men watching. Normally Dean wouldn’t care about their disapproval, but he didn’t want to risk them killing Castiel or Sam. He promised that he would explain everything to Castiel when he woke up, but that was a long time away and right now he had to do what needed to get done to ensure their safety. 

“It means nothing,” he grunted, thrusting deeper into Castiel. “Castiel means nothing to me. Just. Another. Piece. Of. Ass.” He slammed deep with every word, putting on a show for the sicko’s watching. 

Castiel wanted to die. He wanted to just pop out of existence. _Doesn’t Dean know I can hear him? He must know, he has to know. He can’t know. But what if he does. Is this what he’s thinking every time we have sex?_ Castiel shuddered slightly if Dean felt it then he took no notice. _Did he ever love me? Has this whole thing just been a game, a proof of masculinity?_ Dean swore and slapped Castiel's ass hard, "Did he honestly believe he could tame me? I'm Dean. FUCKING. Winchester. And he's just another one of my victims." Dean growled, picking up the speed and brutality of his thrusts. He prayed to whatever gods were listening that the other men would buy the act and let him and Cas go. 

_I really do mean nothing to him. I really am nothing more than just another piece of ass..._ Castiel tried crying out to Dean again, but again no sound escaped his lips. He tried to move his limbs again but they all felt like pieces of lead. He couldn’t do anything except lay there and take it. Lay there and listen as the man he loved, who he thought loved him, raped him. _Please. Stop._ He pleaded, but it was useless.

It felt like a lifetime had passed before Dean came, shuddering deep into Castiel’s ass. Castiel’s pillow was wet with tears, he grimaced when he felt Dean’s lips press gingerly against his back. Mocking all the tender, loving kisses that Dean had placed there before. Mentally and emotionally exhausted, Castiel slipped willingly back into unconsciousness, praying that he would never wake up.

Dean pulled out and got off the bed. “Happy?” he said, “I did what you wanted, now please just let us go home. Castiel needs to be tended to.”

Azazel chuckled, “I don’t know Dean, see the thing about the last demand is that Lucifer said you only had 24 hours to complete the task. It’s been months.”

“You son of a bitch,” Dean growled, “you just forced me to watch you rape the man I love while you raped me, and as if that wasn’t enough I then had to turn around and rape him, and that’s still not enough!? Lucifer Pellegrino named me the head of the Mafia, I completed the task, the twenty four hour timeline has long passed but the fact of the matter is that I raped the warden, made him my little bitch. I am the new leader of the Italian Mafia which means that you are my men.”

Azazel glared, “I don’t think you understand the gravity of the situation. Dick Roman is out for your blood. If he finds out that Castiel is your fuck-buddy,”

“Boyfriend.”

Azazel grimaced, “fine, ‘boyfriend’, although that’s worse. If Roman finds out that you are dating the ex-warden, you can bet your pretty mouth that Castiel will be who Roman sends all of his men after. If you think we’re bad, well. Lets just say that it would be kinder for you to just kill Castiel before Roman’s men got a hold of him. Because of that, I’m afraid we can’t just let you go.”

There was a loud crack and the men watched as Dean crumpled to the floor, Death stood behind him a bat in hand.

**Notes for the Chapter:**

> *hides*
> 
> comments and kudos are greatly appreciated...
> 
> ...Please don't hate me...
> 
> KThanksBye


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